Name: 124931-12-0|Diethyl (2-(methoxy(methyl)amino)-2-oxoethyl)phosphonate|98%
Brand: Ambeed
SKU: A614908
Price: 10.0 USD
Availability: InStock
Rating: 92 (35 reviews)

1
[ 26489-02-1 ]
[ 124931-12-0 ]
[ 141868-91-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature;
50%	With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;

Reference： [1]Netz, David F.; Seidel, Jimmy L. [Tetrahedron Letters, 1992, vol. 33, # 15, p. 1957 - 1958]
[2]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]

2
[ 124931-12-0 ]
[ 432-25-7 ]
[ 141208-06-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With n-butyllithium In tetrahydrofuran; hexane for 24h; Ambient temperature;
	With sodium hydride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
1.43 g	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;

Reference： [1]Groesbeek, M.; Rood, G. A.; Lugtenburg, J. [Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 3, p. 149 - 154]
[2]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]
[3]Livingstone, Keith; Tenberge, Marius; Pape, Felix; Daniliuc, Constantin G.; Jamieson, Craig; Gilmour, Ryan [Organic Letters, 2019, vol. 21, # 23, p. 9677 - 9680]

3
[ 124931-12-0 ]
[ 150943-17-2 ]
[ 153474-56-7 ]
[ 150943-18-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 4.6%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: (2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone In tetrahydrofuran at 20℃; for 14h;
1: 67% 2: 7.7%	In methanol at -78 - 20℃; for 25h;
	With sodium hydride In tetrahydrofuran at 0℃; Yield given. Yields of byproduct given;

Reference： [1]Hanessian, Stephen; Fu, Jian-Min [Canadian Journal of Chemistry, 2001, vol. 79, # 11, p. 1812 - 1826]
[2]Hanessian, Stephen; Fu, Jian-Min [Canadian Journal of Chemistry, 2001, vol. 79, # 11, p. 1812 - 1826]
[3]Hanessian, Stephen; Fu, Jian-Min; Chiara, Jose-Luis; Fabio, Romano Di [Tetrahedron Letters, 1993, vol. 34, # 26, p. 4157 - 4160]

4
[ 124931-12-0 ]
[ 108-94-1 ]
[ 124931-20-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature;
	With n-butyllithium 1.) THF, -78 deg C, 2.) 0 deg C, 1 h; Yield given. Multistep reaction;

Reference： [1]Netz, David F.; Seidel, Jimmy L. [Tetrahedron Letters, 1992, vol. 33, # 15, p. 1957 - 1958]
[2]Nuzillard, Jean-Marc; Boumendjel, Ahcene; Massiot, Georges [Tetrahedron Letters, 1989, vol. 30, # 29, p. 3779 - 3780]

5
[ 124931-12-0 ]
[ 100-52-7 ]
N-methoxy-N-methylcinnamamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: benzaldehyde In tetrahydrofuran at -78 - 20℃;	HWE Reaction; General Procedure A General procedure: Diethyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate (1; 1.2 equiv) was dissolved in anhyd THF and NaH (1.2 equiv) was added portionwise at r.t. until gas evolution ceased. The mixture was then cooled to -78 °C and the appropriate benzaldehyde derivative (1 equiv) dissolved in anhyd THF was added. The reaction mixture was stirred at -78 °C for 1 h, then allowed to warm to r.t. and stirred overnight. H2O (10 mL) was added, the layers were separated, and the organic layer was washed with sat. aq NaHCO3 (2 × 10 mL). The combined aqueous phases were extracted with EtOAc (3 × 15 mL). The combined organic phases were then washed with brine (2 × 10 mL) ,dried (MgSO4), and concentrated in vacuo. If necessary, the crude product was purified by flash column chromatography (FCC) using the indicated eluent.
91%	With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature;

Reference： [1]Glas, Carina; Bracher, Franz [Synthesis, 2019, vol. 51, # 3, p. 757 - 768]
[2]Netz, David F.; Seidel, Jimmy L. [Tetrahedron Letters, 1992, vol. 33, # 15, p. 1957 - 1958]

6
[ 67442-07-3 ]
[ 122-52-1 ]
[ 124931-12-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	at 100℃; for 18h;	A solution of <strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (2.48 g,17.7 mmol) and triethyl phosphite (3.00 mL, 17.7 mmol) was heated to 100 °C for 18 h. The crude product was purified by flash column chromatography (0?2percent MeOH in CH2Cl2) to give 1 as a colorless oil; yield: 3.31 g (13.8 mmol; 78percent); Rf = 0.42 (2percent MeOH in CH2Cl2); HPLC purity (method b): >95percent (210 nm), >95percent (254 nm). IR (ATR): 2985, 2940, 2908, 1659, 1381, 1253, 1050, 1020, 998, 961 cm?1. 1H NMR (400 MHz, CDCl3): delta = 4.26?4.07 (m, 4 H, 2 × OCH2CH3), 3.76(s, 3 H, OCH3), 3.20 (s, 3 H, NCH3), 3.15 (d, J = 22.1 Hz, 2 H, 1-H), 1.33(td, J = 7.1, 0.6 Hz, 6 H, 2 × OCH2CH3). 13C NMR (101 MHz, CDCl3): delta = 166.2 (C-2), 62.7 (2 × OCH2CH3), 61.6(OCH3), 32.3 (NCH3), 30.9 (C-1), 16.5 (2 × OCH2CH3). HRMS (ESI): m/z [M + H]+ calcd for C8H19NO5P+: 240.0995; found: 240.0996.

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 1957 - 1958
[2]Synthesis,2019,vol. 51,p. 757 - 768
[3]Tetrahedron Letters,1989,vol. 30,p. 3779 - 3780

7
[ 124931-12-0 ]
[ 121660-37-5 ]
[ 141750-56-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 350 - 363

8
[ 124931-12-0 ]
[ 33603-83-7 ]
[ 180779-72-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium <i>tert</i>-butylate
80%	With potassium <i>tert</i>-butylate In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) -78 deg C, 1 h;

Reference： [1]Entwistle, David A.; Jordan, Stuart I.; Montgomery, John; Pattenden, Gerald [Journal of the Chemical Society. Perkin transactions I, 1996, # 12, p. 1315 - 1317]
[2]Entwistle, David A.; Jordan, Stuart I.; Montgomery, John; Pattenden, Gerald [Synthesis, 1998, # SPEC. ISS. APR., p. 603 - 612]

9
[ 762-04-9 ]
[ 67442-07-3 ]
[ 124931-12-0 ]

Reference： [1]Synlett,1997,p. 531 - 533

10
[ 124931-12-0 ]
[ 193337-38-1 ]
[ 193337-41-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With n-butyllithium In tetrahydrofuran at 0℃;

Reference： [1]Ouellet; Langlois; Deslongchamps, Pierre [Synlett, 1997, vol. 1997, # 6, p. 689 - 690]

11
[ 124931-12-0 ]
[ 555-16-8 ]
[ 253122-46-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium methylate In tetrahydrofuran at 20℃; for 0.333333h;

Reference： [1]Durantini, Edgardo N. [Synthetic Communications, 1999, vol. 29, # 23, p. 4201 - 4222]

12
[ 124931-12-0 ]
[ 123-11-5 ]
[ 243665-13-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -78 - 20℃;	HWE Reaction; General Procedure A General procedure: Diethyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate (1; 1.2 equiv) was dissolved in anhyd THF and NaH (1.2 equiv) was added portionwise at r.t. until gas evolution ceased. The mixture was then cooled to -78 °C and the appropriate benzaldehyde derivative (1 equiv) dissolved in anhyd THF was added. The reaction mixture was stirred at -78 °C for 1 h, then allowed to warm to r.t. and stirred overnight. H2O (10 mL) was added, the layers were separated, and the organic layer was washed with sat. aq NaHCO3 (2 × 10 mL). The combined aqueous phases were extracted with EtOAc (3 × 15 mL). The combined organic phases were then washed with brine (2 × 10 mL) ,dried (MgSO4), and concentrated in vacuo. If necessary, the crude product was purified by flash column chromatography (FCC) using the indicated eluent.
97%	With sodium methylate In tetrahydrofuran at 20℃; for 0.333333h;
93%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -10 - 20℃; Inert atmosphere;

66%

With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;

Reference： [1]Glas, Carina; Bracher, Franz [Synthesis, 2019, vol. 51, # 3, p. 757 - 768]
[2]Durantini, Edgardo N. [Synthetic Communications, 1999, vol. 29, # 23, p. 4201 - 4222]
[3]Silvanus, Andrew C.; Heffernan, Stephen J.; Liptrot, David J.; Kociok-Koehn, Gabriele; Andrews, Benjamin I.; Carbery, David R. [Organic Letters, 2009, vol. 11, # 5, p. 1175 - 1178]
[4]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]

13
[ 124931-12-0 ]
(2R)-2-benzyloxycarbonylamino-3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tert-butyl ester [ No CAS ]
(2R,3R,4E)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[N-methyl-N-methoxy carbamoyl]pent-4-enoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (2R)-2-benzyloxycarbonylamino-3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tert-butyl ester With diisobutylaluminium hydride In tetrahydrofuran; hexane; toluene at -78 - 20℃;

Reference： [1]David, Christelle; Bischoff, Laurent; Roques, Bernard P.; Fournié-Zaluski, Marie-Claude [Tetrahedron, 2000, vol. 56, # 2, p. 209 - 215]

14
[ 124931-12-0 ]
[ 23637-56-1 ]
(+/-)-N-methoxy-N-methyl-2-(2t-benzoyl-3c-phenylcycloprop-1r-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With methyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 3,6-diphenyl-3,6-dihydro-1,2-dioxine In tetrahydrofuran for 3h; Further stages.;

Reference： [1]Kimber, Marc C.; Taylor, Dennis K. [Journal of Organic Chemistry, 2002, vol. 67, # 9, p. 3142 - 3144]

15
[ 124931-12-0 ]
[ 53646-91-6 ]
trans-(+/-)-N-methoxy-N-methyl-2-(2-benzoylcyclopropyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With methyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 3-phenyl-3,6-dihydro-1,2-dioxine In tetrahydrofuran for 3h; Further stages.;

Reference： [1]Kimber, Marc C.; Taylor, Dennis K. [Journal of Organic Chemistry, 2002, vol. 67, # 9, p. 3142 - 3144]

16
[ 124931-12-0 ]
[ 445306-60-5 ]
[ 445306-61-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydride In tetrahydrofuran at 20℃;
92%	With sodium hydride In tetrahydrofuran at 20℃; for 1.5h;

Reference： [1]Mulzer, Johann; Hanbauer, Martin [Tetrahedron Letters, 2002, vol. 43, # 18, p. 3381 - 3383]
[2]Ahmed, Anjum; Hoegenauer, E. Kate; Enev, Valentin S.; Hanbauer, Martin; Kaehlig, Hanspeter; Ohler, Elisabeth; Mulzer, Johann [Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3026 - 3042]

17
[ 124931-12-0 ]
(2S,4RS)-5-(tert-butyldimethylsilyloxy)-2-methyl-4-(trimethoxymethylphenyl)pentanal [ No CAS ]
[ 478303-49-0 ]
(4S,6S)-7-(tert-butyldimethylsilyloxy)-4-methyl-6-(trimethoxymethylphenyl)hept-2-enoic acid methoxymethylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 57% 2: 35%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: (2S,4RS)-5-(tert-butyldimethylsilyloxy)-2-methyl-4-(trimethoxymethylphenyl)pentanal In tetrahydrofuran at 20℃; for 2.5h;

Reference： [1]Heckrodt, Thilo J.; Mulzer, Johann [Synthesis, 2002, # 13, p. 1857 - 1866]

18
[ 124931-12-0 ]
[ 111865-84-0 ]
[ 526217-80-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 5h;

Reference： [1]Heckrodt, Thilo J.; Mulzer, Johann [Journal of the American Chemical Society, 2003, vol. 125, # 16, p. 4680 - 4681]

19
[ 124931-12-0 ]
C₂₈H₄₄O₁₀ [ No CAS ]
C₃₂H₅₁NO₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.171 g	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: C₂₈H₄₄O₁₀ In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Zakarian, Armen; Batch, Alexandre; Holton, Robert A. [Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7822 - 7824]

20
[ 124931-12-0 ]
[ 623151-46-2 ]
[ 623151-47-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.16667h; Stage #2: (5Z,7E)-(3R,4R)-4-(tert-butyldimethylsilanyloxy)-10-(tert-butyldiphenylsilanyloxy)-3-methyldeca-5,7-dienal In tetrahydrofuran at 20℃; for 1.16667h;

Reference： [1]Dineen, Thomas A.; Roush, William R. [Organic Letters, 2003, vol. 5, # 24, p. 4725 - 4728]

21
[ 862893-91-2 ]
[ 124931-12-0 ]
[ 862893-92-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 2h;

Reference： [1]Sohn, Stephanie S.; Bode, Jeffrey W. [Organic Letters, 2005, vol. 7, # 18, p. 3873 - 3876]

22
[ 863407-41-4 ]
[ 124931-12-0 ]
[ 863407-46-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [6-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

23
[ 863407-42-5 ]
[ 124931-12-0 ]
[ 863407-47-0 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [4-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

24
[ 863407-40-3 ]
[ 124931-12-0 ]
[ 863407-45-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [7-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

25
[ 468718-26-5 ]
[ 124931-12-0 ]
[ 468718-27-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-6-carbonitrile In tetrahydrofuran at 0℃;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

26
[ 863407-39-0 ]
[ 124931-12-0 ]
[ 863407-44-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-4-carbonitrile In tetrahydrofuran at 0℃;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

27
[ 468717-73-9 ]
[ 124931-12-0 ]
[ 468717-74-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 3-formyl-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile In tetrahydrofuran at 0℃; for 1h;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

28
[ 863407-38-9 ]
[ 124931-12-0 ]
[ 863407-43-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-7-carbonitrile In tetrahydrofuran at 0℃;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

29
[ 124931-12-0 ]
[ 217489-00-4 ]
[ 468717-78-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 5-fluoro-1-(p-tolylsulfonyl)indole-3-carboxaldehyde In tetrahydrofuran at 0℃;
88%	In tetrahydrofuran	2 Trans-1-(N,N-dimethylaminomethyl)-2-[5-fluoroindol-3-yl]cyclopropane A solution of diethyl (N-methoxy-N-methylcarbamoylmethyl) phosphonate (5.64 ml, 6.54 g, 27.4 mmol) in anhydrous tetrahydrofuran (25 ml) was added to a stirred suspension of oil free sodium hydride (1.05 g, 27.4 mmol) in anhydrous tetrahydrofuran (350 ml) maintained at 0° C. The reaction was warmed to room temperature and was stirred for 2 h. After cooling to 0° C., [5-fluoro-1-(p-toluenesulfonyl)indol-3-yl]carboxaldehyde (7.24 g, 22.8 mmol) was added. The resulting mixture was stirred at 0° C. for 30 min. The reaction was quenched with aqueous hydrochloric acid (0.1 N) and poured into water (150 ml). After being made acidic with hydrochloric acid (1.0 N), the aqueous portion was extracted with ethyl acetate (3*100 ml). The combined organic layers were washed with brine (50 ml) and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo. The crude product was purified by recrystallization from ethyl acetate to afford a total of 8.03 g (88% yield) of (E)-[5-fluoro-1-(p-toluenesulfonyl)indol-3-yl]-N-methoxy-N-methylacrylamide as a white solid: mp 199-200° C. (dec.); 1H NMR (400 MHz, DMSO-d6) 8.56 (1 H, s), 7.99 (1 H, m), 7.93 (2 H, d, J=8.4 Hz), 7.68 (2 H, m), 7.42 (2 H, d, J=8.1 Hz), 7.28 (1 H, t, J=9.2 Hz), 7.12 (1 H, d, J=16 Hz), 3.77 (3 H, s), 3.22 (3 H, s), 2.33 (3 H, s); MS m/e 403 (M+H)+. Anal. Calcd. For C20H19FN2O4S: C, 59.69; H, 4.75; N 6.96. Found: C, 59.60; H, 4.70; N, 6.86.

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2003/73849, 2003, A1

30
[ 124931-12-0 ]
[ 1489-69-6 ]
[ 141580-89-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: Cyclopropanecarboxaldehyde In tetrahydrofuran at 20℃; for 2h; Further stages.;
79%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Cyclopropanecarboxaldehyde In tetrahydrofuran at 20℃; for 4h;

Reference： [1]Wender, Paul A.; Fuji, Masahiro; Husfeld, Craig O.; Love, Jennifer A. [Organic Letters, 1999, vol. 1, # 1, p. 137 - 139]
[2]Trost, Barry M.; Shen, Hong C.; Horne, Daniel B.; Toste, F. Dean; Steinmetz, Bernhard G.; Koradin, Christopher [Chemistry - A European Journal, 2005, vol. 11, # 8, p. 2577 - 2590]

31
[ 20780-76-1 ]
[ 124931-12-0 ]
(E)-2-(5-iodo-2-oxoindolin-3-ylidene)-N-methoxy-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 18h;

Reference： [1]Chen, Chuo; Li, Xiaodong; Neumann, Christopher S.; Lo, Michael M.-C.; Schreiber, Stuart L. [Angewandte Chemie - International Edition, 2005, vol. 44, # 15, p. 2249 - 2252]

32
[ 124931-12-0 ]
[ 689258-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH In tetrahydrofuran	63.3 (2-{2,3-Difluoro-4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}cyclopropyl)acetic acid Trifluoroacetate. Step 3: (2E)-3-(2,3-Difluoro-4-methoxyphenyl)-N-methoxy-N-methylprop-2-enamide. Diethyl (N-methoxy-N-methylcarbamoylmethyl)-phosphonate (4.8 g) was added to a suspension of 95% NaH (550 mg) in THF (40 mL) under nitrogen atmosphere. The mixture was stirred at an ambient temperature for 10 minutes, and was treated with the product of step 2 (3.44 grams). The mixture was stirred at room temperature for 1 hour and was quenched with water (10 mL). The mixture was concentrated in vacuoo afforded an oily residue. The residue was extracted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated to yield 3.2 grams of the title compound as white solid. 1H-NMR(CDCl3): 7.72 (d, 1H), 7.22(m, 1H), 7.15(d, 1H), 6.75(m,1H), 3.92(s, 3H), 3.78(s, 3H), 3.3(s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - US6921767, 2005, B2

33
[ 124931-12-0 ]
[ 225786-18-5 ]
C₁₂H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.4 g	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; Stage #2: (S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)ethanal In tetrahydrofuran at 0 - 20℃; Further stages.;
13.4 g	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 24℃; Inert atmosphere; Stage #2: (S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)ethanal In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere;

Reference： [1]Lu, Chong-Dao; Zakarian, Armen [Organic Letters, 2007, vol. 9, # 16, p. 3161 - 3163]
[2]Araoz, Romulo; Servent, Denis; Molgoi, Jordi; Iorga, Bogdan I.; Fruchart-Gaillard, Carole; Benoit, Evelyne; Gu, Zhenhua; Stivala, Craig; Zakarian, Armen [Journal of the American Chemical Society, 2011, vol. 133, # 27, p. 10499 - 10511]

34
[ 124931-12-0 ]
[ 939795-56-9 ]
(2E,4S,5S,6S)-N-methyl-N-methoxy-7-(tert-butyldimethylsilyloxy)-4,6-dimethyl-5-hydroxy-hept-2-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.75h;
86%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: (2R,3R,4S)-5-(tert-butyldimethylsilyloxy)-2,4-dimethyl-3-hydroxy-pentanal In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;

Reference： [1]De Lemos, Elsa; Poree, Francois-Hugues; Commercon, Alain; Betzer, Jean-Francois; Pancrazi, Ange; Ardisson, Janick [Angewandte Chemie - International Edition, 2007, vol. 46, # 11, p. 1917 - 1921]
[2]Location in patent: experimental part De Lemos, Elsa; Poree, Francois-Hugues; Bourin, Arnaud; Barbion, Julien; Agouridas, Evangelos; Lannou, Marie-Isabelle; Commercon, Alain; Betzer, Jean-Francois; Pancrazi, Ange; Ardisson, Janick [Chemistry - A European Journal, 2008, vol. 14, # 35, p. 11092 - 11112]

35
[ 124931-12-0 ]
[ 6188-43-8 ]
C₁₂H₁₃N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5647 - 5651

36
[ 5381-20-4 ]
[ 124931-12-0 ]
[ 468718-37-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5647 - 5651

37
[ 124931-12-0 ]
[ 209256-42-8 ]
[ 209256-81-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 18h;	Diethyl (N-methoxy-N-methyl-carbamoylmethyl) phosphonate (4.0 g, 16.7 mmol) was added dropwise to a suspension of sodium hydride (671 mg, 60% dispersion in mineral oil, 16.7 mmol) in THF (75 mL) at 0C. A solution of <strong>[209256-42-8]2,3-dihydrobenzofuran-4-carboxaldehyde</strong> (3.0 g, 15.2 mmol) in THF (25 mL) was added dropwise. The resulting suspension was allowed to warm to room temperature. After 18 h, water (60 mL) was added and the solution was extracted three times with ethyl acetate. The organic extracts were combined, washed with water and brine, dried over K2CO3, and concentrated to give a pale red oil, 3.5 g (100%).

Reference： [1]Patent: EP1027043,2004,B1 .Location in patent: Page/Page column 24

38
[ 124931-12-0 ]
[ 101125-34-2 ]
[ 375846-19-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium In tetrahydrofuran; water; pentane	12 (E)-3-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-N-methoxy-N-methylacrylamide EXAMPLE 12 (E)-3-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-N-methoxy-N-methylacrylamide 0.465 g (10.65 mmol) of sodium hydride (55%) are introduced into a 100 ml three-necked, round-bottomed flask, equipped with a magnetic stirrer, thermometer, dropping funnel and nitrogen delivery line, and washed twice with 5 ml of pentane. The pentane is removed using a pipette and the sodium hydride is blown dry with nitrogen. 10 ml of THF, rendered absolute using sodium, are added, and 1.84 g (7.46 mmol) of diethyl (N-methoxy-N-methylcarbamoyl-methyl)phosphonate dissolved in 5 ml of THF are slowly added dropwise so that the temperature does not exceed 30° C. 1 g (3.55 mmol) of 3-(4-fluorophenyl)-1-isopropyl-1H-indole-2-carbaldehyde dissolved in 10 ml of THF is then added dropwise and the clear, slightly yellow solution is stirred overnight. The reaction mixture is poured into 100 ml of water and extracted 3 times with 50 ml of ethyl acetate. The combined organic phases are washed twice with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated by evaporation. Flash chromatography (hexane/ethyl acetate=2:1) and crystallisation from 94% ethanol yields slightly yellow crystals having a melting point of from 123 to 124° C.

Reference： [1]Current Patent Assignee: BASF SE - US2003/166946, 2003, A1

39
[ 871094-94-9 ]
[ 124931-12-0 ]
[ 917483-65-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; for 0.75h; Stage #2: (1R,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalene-1-carbaldehyde In tetrahydrofuran at 20℃; Further stages.;

Reference： [1]Sheddan, Neil A.; Mulzer, Johann [Organic and Biomolecular Chemistry, 2006, vol. 4, # 22, p. 4127 - 4130]

40
[ 124931-12-0 ]
[ 22062-53-9 ]
[ 1019841-01-0 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 4978 - 4983

41
[ 124931-12-0 ]
[ 104501-60-2 ]
[ 1012041-69-8 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With lithium hydroxide; 4 A molecular sieve In tetrahydrofuran at 40℃; for 0.333333h; Stage #2: 2-tert-butyldimethylsilyloxypropanal In tetrahydrofuran at 0 - 20℃; Stage #3: With hydrogenchloride In isopropyl alcohol at 20℃; Further stages.;

Reference： [1]Son, Sunghee; Fu, Gregory C. [Journal of the American Chemical Society, 2008, vol. 130, # 9, p. 2756 - 2757]

42
[ 124931-12-0 ]
[ 104-87-0 ]
[ 141750-54-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
80%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran at -10 - 20℃; Inert atmosphere;

Reference： [1]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]
[2]Silvanus, Andrew C.; Heffernan, Stephen J.; Liptrot, David J.; Kociok-Koehn, Gabriele; Andrews, Benjamin I.; Carbery, David R. [Organic Letters, 2009, vol. 11, # 5, p. 1175 - 1178]

43
[ 124931-12-0 ]
[ 104-88-1 ]
[ 771557-40-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran at -10 - 20℃; Inert atmosphere;
74%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran at -78 - 20℃;	HWE Reaction; General Procedure A General procedure: Diethyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate (1; 1.2 equiv) was dissolved in anhyd THF and NaH (1.2 equiv) was added portionwise at r.t. until gas evolution ceased. The mixture was then cooled to -78 °C and the appropriate benzaldehyde derivative (1 equiv) dissolved in anhyd THF was added. The reaction mixture was stirred at -78 °C for 1 h, then allowed to warm to r.t. and stirred overnight. H2O (10 mL) was added, the layers were separated, and the organic layer was washed with sat. aq NaHCO3 (2 × 10 mL). The combined aqueous phases were extracted with EtOAc (3 × 15 mL). The combined organic phases were then washed with brine (2 × 10 mL) ,dried (MgSO4), and concentrated in vacuo. If necessary, the crude product was purified by flash column chromatography (FCC) using the indicated eluent.

Reference： [1]Silvanus, Andrew C.; Heffernan, Stephen J.; Liptrot, David J.; Kociok-Koehn, Gabriele; Andrews, Benjamin I.; Carbery, David R. [Organic Letters, 2009, vol. 11, # 5, p. 1175 - 1178]
[2]Glas, Carina; Bracher, Franz [Synthesis, 2019, vol. 51, # 3, p. 757 - 768]

44
[ 124931-12-0 ]
[ 529-20-4 ]
[ 1019840-98-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: 2-methylphenyl aldehyde In tetrahydrofuran at -10 - 20℃; Inert atmosphere;

Reference： [1]Silvanus, Andrew C.; Heffernan, Stephen J.; Liptrot, David J.; Kociok-Koehn, Gabriele; Andrews, Benjamin I.; Carbery, David R. [Organic Letters, 2009, vol. 11, # 5, p. 1175 - 1178]

45
[ 124931-12-0 ]
[ 220861-39-2 ]
C₁₅H₂₉NO₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 23℃;	2 To the solution of the ester prepared in the precedent procedure (5.85 g, 20.4 mmol) in CH2CI2 (100 mL) under nitrogen atmosphere, DIBAL (24.5 mL, IM in toluene, 1.2 equiv.) was added at -78 0C and the reaction was kept stirring at the same temperature for half an hour. Then saturated tartrate salt solution (100 mL) was added to the reaction and stirred for 2 hrs until the system turned clear. The two phases were separated and extracted by CH2CI2 (100 mL x 2), washed by brine, dried over Na2SO4. After removal of the solvent, the residue (4.33 g) obtained was used for the next step without further purification. To the solution of the aldehyde (4.33 g) in CH2Cl2 (100 mL) was added Wittig reagent (7.33g, 20.2 mmol, 1.0 equiv.) at 23 0C. The reaction was stirred overnight. After removal of the solvent under reduced vacuum, the residue underwent flash chromatography (PE/EA = 20: 1, then 10/1, 3/1) afforded the desired compound (4.25 g) in the yield of 71 % for the two steps. 1H (CDCI3, 400 MHz, 25 0C) δ 6.89-6.96 (dt, IH); 6.41 (d, IH); 5.77-5.85 (m, IH); 5.18 (dd, IH); 5.05 (dd, IH); 4.23 (dd, IH); 3.67 (s, 3H); 3.22 (s, 3H); 2.42 (dd, 2H); 0.88 (s, 9H); 0.03 (d, 6H).13C (CDCl3, 400 MHz, 25 0C) δ 166.6, 143.5, 140.6, 120.9, 114.3, 72.7, 61.6, 41.4, 32.3, 25.8, 18.2, -4.5, -4.9.

Reference： [1]Current Patent Assignee: UNIVERSITY OF STRASBOURG - WO2009/91921, 2009, A1 Location in patent: Page/Page column 88; 97

46
[ 124931-12-0 ]
[ 256417-11-5 ]
[ 689258-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2,3-difluoro-4-methoxy-benzaldehyde In tetrahydrofuran at 20℃; for 1h;	63.3 Diethyl (N-methoxy-N-methylcarbamoylmethyl)-phosphonate (4.8 g) was added to a suspension of 95% NaH (550 mg) in THF (40 mL) under nitrogen atmosphere. The mixture was stirred at an ambient temperature for 10 minutes, and was treated with the product of step 2 (3.44 grams). The mixture was stirred at room temperature for 1 hour and was quenched with water (10 mL). The mixture was concentrated in vacuoo afforded an oily residue. The residue was extracted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated to yield 3.2 grams of the title compound as white solid. 1HNMR(CDCl3): 7.72 (d, 1H), 7.22(m, 1H), 7.15(d, 1H), 6.75(m,1H), 3.92(s, 3H), 3.78(s, 3H), 3.3(s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2004/92538, 2004, A1 Location in patent: Page 58

47
[ 1173891-73-0 ]
[ 124931-12-0 ]
[ 1007313-82-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 23℃; for 0.75h; Inert atmosphere;

Reference： [1]Wang, Cuihua; Barluenga, Sofia; Koripelly, Girish K.; Fontaine, Jean-Gonzague; Chen, Ruihong; Yu, Jin-Chen; Shen, Xiaodong; Chabala, John C.; Heck, James V.; Rubenstein, Allan; Winssinger, Nicolas [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 14, p. 3836 - 3840]

48
[ 124931-12-0 ]
[ 667419-29-6 ]
[ 1204185-43-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: 7-(4-methoxyphenylmethoxy)heptanal In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere;

Reference： [1]Sui, Bin; Yeh, Edmund A.-H.; Curran, Dennis P. [Journal of Organic Chemistry, 2010, vol. 75, # 9, p. 2942 - 2954]

49
[ 112-45-8 ]
[ 124931-12-0 ]
[ 1222465-49-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: 10-Undecenal In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h;

Reference： [1]Donohoe, Timothy J.; Bower, John F. [Proceedings of the National Academy of Sciences of the United States of America, 2010, vol. 107, # 8, p. 3373 - 3376]

50
[ 124931-12-0 ]
[ 144681-67-4 ]
C₁₅H₃₁NO₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With barium(II) hydroxide In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere; Stage #2: 3-(tert-butyldimethylsilanyloxy)-2,2-dimethylpropionaldehyde In tetrahydrofuran; water at 20℃; for 24h; Inert atmosphere;
	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 3-(tert-butyldimethylsilanyloxy)-2,2-dimethylpropionaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃;

Reference： [1]Trost, Barry M.; Yang, Hanbiao; Dong, Guangbin [Chemistry - A European Journal, 2011, vol. 17, # 35, p. 9789 - 9805]
[2]Nguyen, Xuan B.; Nakano, Yuji; Duggan, Nisharnthi M.; Scott, Lydia; Breugst, Martin; Lupton, David W. [Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11483 - 11490][Angew. Chem., 2019, vol. 131, # 33, p. 11607 - 11614]

51
[ 124931-12-0 ]
[ 122606-77-3 ]
[ 1222190-46-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: (R)-4-hydroxy-1-undecene With ozone In dichloromethane at -78℃; for 0.0833333h; Stage #2: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In dichloromethane; acetonitrile at 20℃; for 18h;

Reference： [1]Yadav; Rajendar, Goreti [European Journal of Organic Chemistry, 2011, # 33, p. 6781 - 6788]

52
[ 3095-95-2 ]
[ 6638-79-5 ]
[ 124931-12-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 12h;
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;

Reference： [1]Location in patent: experimental part Barthes, Nicolas; Grison, Claude [Bioorganic Chemistry, 2012, vol. 40, # 1, p. 48 - 56]
[2]Livingstone, Keith; Tenberge, Marius; Pape, Felix; Daniliuc, Constantin G.; Jamieson, Craig; Gilmour, Ryan [Organic Letters, 2019, vol. 21, # 23, p. 9677 - 9680]

53
[ 124931-12-0 ]
[ 133271-07-5 ]
[ 1374348-48-7 ]

Yield	Reaction Conditions	Operation in experiment
491 mg	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 0℃; for 0.333333h; Stage #2: C₁₁H₁₂O₂ In acetonitrile at 20℃; for 4h;	(S,2E,6E)-5-hydroxy-N-methoxy-N-methyl-7-phenylhepta-2,6-dienamide (21). To a stirred solution of 10 (1 g, 2.61 mmol) in dry THF (20 mL) was added asolution of DIBAL-H in toluene (4.4 mL, 7.83 mmol, 25% solution in toluene) at -78 oC, and allowed to stir for 30 min at same temperature. Then the reaction was quenched by adding saturated sodiumpotassiumtartarate solution (10 mL). The resultant mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered and evaporated. The resulting crude product 390 mg was employed in next step without further purification. To a stirred solution of (OEt)2P(O)CH2C(O)NMe(OMe) (794 mg, 3.32 mmol) in CH3CN (15 ml) was added LiCl (140 mg, 3.32 mmol) and DBU (0.494 ml, 3.32 mmol) at 0 oC and the mixture was stirred for 20 minutes and the aldehyde (390 mg, 2.215 mmol ) in CH2Cl2 (5 mL) was added dropwise at 0 oC and the reaction mixture was stirred for 4 h at room temperature. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, evaporated under reduced pressure and purified by column chromatography (60-120 silica gel) using EtOAc/hexane (40%) as an eluent to afford 21 (491 mg, 78%) as yellow liquid. Rf = 0.5 (60% EtOAc/hexane). IR (neat) υmax : 3405, 2931, 1659, 1618, 1448, 1387, 970 cm-1; 1H NMR (500 MHz, CDCl3) : δ 7.32-7.13 (m, 5H), 6.92 (dt, J = 15.0, 7.0 Hz, 1H), 6.54 (d, J = 16.0 Hz, 1H), 6.44 (d, J = 15.0 Hz, 1H), 6.17 (dd, J = 15.0, 6.0 Hz, 1H), 4.38 (q, J = 13.0, 6.0 Hz, 1H), 3.58 (s, 3H), 3.15 (s, 3H), 2.50 (m, 2H); 13C NMR (75 MHz, CDCl3) : δ 166.5, 143.1, 136.4, 131.2, 130.4, 128.4, 127.6, 126.4, 121.4, 71.3, 61.6, 40.5, 32.2; Mass (ESI-MS) m/z : 284 [M + Na]+; HRMS (ESI) : Calcd. for C15H19NO3Na 284.1262, found 284.1280.

Reference： [1]Yadav; Bhunia, Dinesh C.; Ganganna [Tetrahedron Letters, 2012, vol. 53, # 20, p. 2496 - 2499]

54
[ 866324-09-6 ]
[ 124931-12-0 ]
[ 1384193-05-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 0.333333h; Inert atmosphere; Stage #2: (3R,5R,6E)-3,5--butyl(dimethyl)silyl]oxy}-7-phenylhept-6-enal In dichloromethane; acetonitrile at 20℃; for 1h; Inert atmosphere;

Reference： [1]Yadav, Jhillusingh; Ganganna, Bogonda; Bhunia, Dineshchandra [Synthesis, 2012, vol. 44, # 9, p. 1365 - 1372]

55
[ 124931-12-0 ]
3-(tert-butyldimethylsilyloxy)-20-((oxomethyl)methylene)pregn-5-ene [ No CAS ]
[ 1384735-81-2 ]
[ 1384736-29-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 24%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 3-(tert-butyldimethylsilyloxy)-20-((oxomethyl)methylene)pregn-5-ene In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	4.2.1. (20E,23E)-N-Methoxy-N-methyl-24-(3β-(tert-butyldimethylsilyloxy)-chola-5,20(22),23-triene)carboxamide and [(20E,23E)-17] and (20Z,23E)-N-methoxy-N-methyl-24-(3β-(tert-butyldimethylsilyloxy)-chola-5,20(22),23-triene)carboxamide [(20Z,23E)-17] NaH (60% dispersion in mineral oil, 190 mg, 4.75 mmol) was added portion-wise to a solution of diethyl 2-(methoxy(methyl)amino)-2-oxoethylphosphonate30 (16) (1.030 g, 4.31 mmol) in anhydrous THF (15 mL) stirring under a N2 atmosphere at 0 °C. The mixture was stirred for a further 10 min following the completion of effervescence of H2 then a solution of isomeric aldehydes (20E)-15 and (20Z)-15 (∼75%:25%, 912 mg, 2.00 mmol) in anhydrous THF (10 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature and was stirred for 16 h. Saturated aqueous NH4Cl solution (10 mL) was added to quench the reaction and the aqueous and organic layers were separated. The aqueous layer was extracted with CH2Cl2 (3 × 20 mL). The combined organic extract was washed with brine (20 mL), dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 100% CH2Cl2 to 2% EtOAc in CH2Cl2) to afford the major unsaturated Weinreb amide (20E,23E)-17 (810 mg, 1.49 mmol, 75%) and the minor isomer (20Z,23E)-17 (261 mg, 0.48 mmol, 24%; total 99% yield) as white solids.

Reference： [1]Location in patent: experimental part Johnston, Jonathan B.; Singh, Arti A.; Clary, Anaelle A.; Chen, Chiung-Kuan; Hayes, Patricia Y.; Chow, Sharon; De Voss, James J.; Ortiz De Montellano, Paul R. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 13, p. 4064 - 4081]

56
[ 124931-12-0 ]
[ 1416466-41-5 ]
C₂₇H₃₉NO₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride In tetrahydrofuran at -78 - -40℃; for 1h; Inert atmosphere;

Reference： [1]Gajula, Praveen Kumar; Sharma, Shrikant; Ampapathi, Ravi Sankar; Chakraborty, Tushar Kanti [Organic and Biomolecular Chemistry, 2013, vol. 11, # 2, p. 257 - 260]

57
[ 124931-12-0 ]
C₃₉H₅₃FN₄O₁₀ [ No CAS ]
C₄₃H₆₀FN₅O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: C₃₉H₅₃FN₄O₁₀ In tetrahydrofuran at 20℃; for 2h;	13 To a solution of diethyl (2-(methoxy(methyl)amino)-2-oxoethyl)phosphonate (91 mg, 0.368 mmol) in THF (5.0 mL) was added NaH (2.8 mg, 0.1 104 mmol) in anhydrous THF (0.2 mL) at 0 °C with stirring. The solution was then stirred at 20°C until it became clear. Then 23-3 (70 mg, 0.092 mmol) was added to the clear solution and the mixture stirred at 20 °C for 2 h. The mixture was quenched with water (10 mL) and extracted with ethyl acetate (3 x 30 mL). The organic layer was washed with brine and dried over Na2S04, filtered and reduced in vacuo. The residue was purified by preparative HPLC to obtained 23 as a white solid.

Reference： [1]Current Patent Assignee: ABLIVA AB - WO2013/61052, 2013, A1 Location in patent: Page/Page column 87-88

58
[ 124931-12-0 ]
C₃₉H₅₂F₂N₄O₁₀ [ No CAS ]
C₄₃H₅₇F₂N₅O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: C₃₉H₅₂F₂N₄O₁₀ In tetrahydrofuran at 20℃; for 2h;	20 xample 20 - preparation of compound 30 xample 20 - preparation of compound 30 To a solution of diethyl (2-(methoxy(methyl)amino)-2-oxoethyl)phosphonate (37 mg, 0.155 mmol) in THF (1.0 mL) was added NaH (2.3 mg, 0.0575 mmol) in anhydrous THF (0.2 mL) at 0 °C with stirring. The solution was then stirred at 20 °C until it became clear. Then 28-3 (30 mg, 0.0387 mmol) was added to the clear solution and the mixture stirred at 20 °C for 2 h. The mixture was quenched with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The organic layer was washed with brine and dried over Na2S04, filtered, evaporated. The residue was purified by preparative HPLC to obtained 30 as a white solid.

Reference： [1]Current Patent Assignee: ABLIVA AB - WO2013/61052, 2013, A1 Location in patent: Page/Page column 93

59
[ 124931-12-0 ]
C₃₉H₅₃FN₄O₁₀ [ No CAS ]
C₄₃H₆₀FN₅O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h;	13 Example 13 Preparation of Compound 23 To a solution of diethyl (2-(methoxy(methyl)amino)-2-oxoethyl)phosphonate (91 mg, 0.368 mmol) in THF (5.0 mL) was added NaH (2.8 mg, 0.1104 mmol) in anhydrous THF (0.2 mL) at 0° C. with stirring. The solution was then stirred at 20° C. until it became clear. Then 23-3 (70 mg, 0.092 mmol) was added to the clear solution and the mixture stirred at 20° C. for 2 h. The mixture was quenched with water (10 mL) and extracted with ethyl acetate (3×30 mL). The organic layer was washed with brine and dried over Na2SO4, filtered and reduced in vacuo. The residue was purified by preparative HPLC to obtained 23 as a white solid.

Reference： [1]Current Patent Assignee: ABLIVA AB - US2014/234414, 2014, A1 Location in patent: Paragraph 0389; 0392

60
[ 124931-12-0 ]
C₃₉H₅₂F₂N₄O₁₀ [ No CAS ]
C₄₃H₅₉F₂N₅O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h;	20 Example 20 Preparation of Compound 30 To a solution of diethyl (2-(methoxy(methyl)amino)-2-oxoethyl)phosphonate (37 mg, 0.155 mmol) in THF (1.0 mL) was added NaH (2.3 mg, 0.0575 mmol) in anhydrous THF (0.2 mL) at 0° C. with stirring. The solution was then stirred at 20° C. until it became clear. Then 28-3 (30 mg, 0.0387 mmol) was added to the clear solution and the mixture stirred at 20° C. for 2 h. The mixture was quenched with water (10 mL) and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine and dried over Na2SO4, filtered, evaporated. The residue was purified by preparative HPLC to obtained 30 as a white solid

Reference： [1]Current Patent Assignee: ABLIVA AB - US2014/234414, 2014, A1 Location in patent: Paragraph 0409; 0410

61
[ 124931-12-0 ]
C₁₅H₃₀O₄Si [ No CAS ]
C₁₉H₃₇NO₅Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: C₁₅H₃₀O₄Si In tetrahydrofuran; mineral oil at 20℃; for 3h; Inert atmosphere;	To a solution of phosphate 19 (23.9 g, 100.1 mmol) in THF (130 mL) was slowly added NaH (4.17g, 95.6 mmol, 55% dispersion in mineral oil) at 0 C, and the mixture was stirredfor 1 h. To this was added a solution of aldehyde 18 (27.5 g, 91.0 mmol) in THF (100 mL), and the mixture was stirredfor 3 h at room temperature. A saturated aqueous NH4Cl solution wasadded, and the mixture was separated. The aqueous layer was extracted with ethylacetate, and the combined organic layers were washed with brine, dried overanhydrous MgSO4, and concentrated under reduced pressure. Theresidue was purified by silica gel column chromatography (ethyl acetate/hexane)to afford amide 20 (32.6 g, 92%) as acolorless oil: IR (neat) νmax 2970,2891, 1664, 1634, 1462, 1381, 1161, 1105, 1068, 1037, 928, 683 cm-1;1H NMR (500 MHz, CDCl3)δ 6.77 (d, J = 16.0 Hz, 1H), 6.60 (d,J = 16.0 Hz, 1H), 4.94 (d, J = 6.3 Hz, 1H), 4.71 (d, J = 6.3 Hz, 1H), 4.01 (d, J = 11.5 Hz, 2H), 3.94 (s, 2H),3.70-3.67 (m, 5H, involving a singlet at 3.69), 3.25 (s, 3H), 1.16-1.05 (m,21H); 13C NMR (125 MHz, CDCl3) δ 145.83,119.88, 93.97, 70.34, 64.18, 61.69, 42.15, 17.97, 11.88 (2C missing); HRMS (FI+) calcd for C19H37NO5Si [M]+: 387.2441, found: 387.2431.

Reference： [1]Sakurai, Kentaro; Tanino, Keiji [Tetrahedron Letters, 2015, vol. 56, # 3, p. 496 - 499]

62
[ 142-83-6 ]
[ 124931-12-0 ]
(2E,4E,6E)-N-methoxy-N-methyl-octa-2,4,6-trienamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1.08333h; Inert atmosphere; Darkness; Stage #2: trans,trans-2,4-Hexadienal In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Darkness;

Reference： [1]Olson, Andrew S.; Chen, Haotong; Du, Liangcheng; Dussault, Patrick H. [RSC Advances, 2015, vol. 5, # 15, p. 11644 - 11648]

63
[ 16326-86-6 ]
[ 124931-12-0 ]
(2E,4E,6E,8E)-N-methoxy-N-methyl-deca-2,4,6,8-tetraenamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1.08333h; Inert atmosphere; Darkness; Stage #2: (2E,4E,6E)-2,4,6-octatrienal In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Darkness;

Reference： [1]Olson, Andrew S.; Chen, Haotong; Du, Liangcheng; Dussault, Patrick H. [RSC Advances, 2015, vol. 5, # 15, p. 11644 - 11648]

64
[ 887267-04-1 ]
[ 124931-12-0 ]
(E)-3-(3,6-difluoro-2-methoxyphenyl)-N-methoxy-N-methylacrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In diethyl ether; mineral oil at 0℃; for 0.5h; Stage #2: 3,6-difluoro-2-methoxybenzaldehyde In diethyl ether; mineral oil at 0 - 20℃; for 18h;	AN.AN1 Step AN1. A 60 % dispersion of sodium hydride in mineral oil (0.906 g, 37.8 mmol) was added to a chilled 0 °C solution of diethyl (2-(methoxy(methyl)amino)-2- oxoethyl)phosphonate (7.64 g, 32.0 mmol) in diethyl ether (250 mL). After 30 minutes, 3,6-difluoro-2-methoxybenzaldehyde (5.0 g, 29.0 mmol) was slowly added. The resulting mixture was allowed to warm to rt and stir for 18 h. The reaction was quenched with IN HC1 (10 mL), then poured into water. The aqueous layer was made acidic with IN HC1 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product mixture was purified by silica-gel column chromatography (0-50% EtOAc/hexanes) to afford (E)-3-(3,6-difluoro-2-methoxyphenyl)-N-methoxy- N-methylacrylamide (4.96 g, 66 % yield). LC-MS (M+H)+ 258.1.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/42243, 2015, A1 Location in patent: Page/Page column 47

65
[ 124931-12-0 ]
[ 74-88-4 ]
[1-(methoxy-methyl-carbamoyl)-ethyl]-phosphonic acid diethylester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 18h;	Diethyl 1-mehtyl-(N-methoxy-N-methylcarbamoylmethyl)phosphonate (S5) A solution of S49 (1.08 g, 4.53 mmol) in THF (2.0 mL) was added dropwise to a suspension of NaH (60% in mineral oil, 217.6 mg, 5.44 mmol) in THF (6.5 mL) at 0 °C. After the reaction mixture was stirred for 30 min, methyl iodide (0.85 mL, 13.7 mmol) was added dropwise to the reaction mixture at 0 °C. The mixture was stirred 0 °C to room temperature for 18 h and quenched with sat. NH4Cl, and extracted with CH2Cl2. The combined organic layer was washed with water and brine, dried over Na2SO4, and evaporated under reduced pressure. The residue was distilled by bulb to bulb distillation to give S510 (770.3 mg,72%) as a colorless oil. 1H NMR (500 MHz, CDCl3) 4.18-4.12 (m, 4H), 3.77 (s, 3H), 3.73-3.62 (m, 1H), 3.23 (bs, 3H), 1.43 (dd, J = 18.4, 7.2 Hz, 3H), 1.34 (t, J = 7.1 Hz, 6H).

Reference： [1]Takagi, Ryukichi; Tanaka, Kenji; Yamamoto, Koumei; Hiraga, Yoshikazu; Kojima, Satoshi; Abe, Manabu [Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 1, p. 146 - 148]

66
[ 2385-77-5 ]
[ 124931-12-0 ]
(R,E)-N-methoxy-N,5,9-trimethyldeca-2,8-dienamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;

Reference： [1]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]

67
[ 5949-05-3 ]
[ 124931-12-0 ]
(S,E)-N-methoxy-N,5,9-trimethyldeca-2,8-dienamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;

Reference： [1]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]

68
[ 124931-12-0 ]
[ 590-86-3 ]
[ 1067975-09-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;
53%	With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h;

Reference： [1]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]
[2]Arseniyadis, Stellios; Campagne, Jean-Marc; Lauberteaux, Jimmy; Lebrun, Aurélien; Mansot, Justine; Marcia de Figueiredo, Renata; Mauduit, Marc; Smietana, Michael; Vasseur, Jean-Jacques [Chemistry - A European Journal, 2020]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	124931-12-0	MDL No. :	MFCD00134233
Formula :	C₈H₁₈NO₅P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WYLRYBDGIILFIR-UHFFFAOYSA-N
M.W :	239.21	Pubchem ID :	2773719
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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P250	Do not subject to grinding/shock/friction.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
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P305	IF IN EYES:
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P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
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P342	If experiencing respiratory symptoms:
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P411
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 124931-12-0 ]

Quality Control of [ 124931-12-0 ]

Related Doc. of [ 124931-12-0 ]

Product Details of [ 124931-12-0 ]

Safety of [ 124931-12-0 ]

Application In Synthesis of [ 124931-12-0 ]

[ 124931-12-0 ] Synthesis Path-Downstream 1~68

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry