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[ CAS No. 504-63-2 ] {[proInfo.proName]}

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Chemical Structure| 504-63-2
Chemical Structure| 504-63-2
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Product Details of [ 504-63-2 ]

CAS No. :504-63-2 MDL No. :MFCD00002949
Formula : C3H8O2 Boiling Point : -
Linear Structure Formula :CH2(CH2OH)2 InChI Key :YPFDHNVEDLHUCE-UHFFFAOYSA-N
M.W : 76.09 Pubchem ID :10442
Synonyms :

Calculated chemistry of [ 504-63-2 ]

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 18.86
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.02
Log Po/w (XLOGP3) : -1.04
Log Po/w (WLOGP) : -0.64
Log Po/w (MLOGP) : -0.63
Log Po/w (SILICOS-IT) : -0.37
Consensus Log Po/w : -0.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.48
Solubility : 227.0 mg/ml ; 2.99 mol/l
Class : Highly soluble
Log S (Ali) : 0.68
Solubility : 363.0 mg/ml ; 4.77 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.18
Solubility : 117.0 mg/ml ; 1.53 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 504-63-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 504-63-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 504-63-2 ]
  • Downstream synthetic route of [ 504-63-2 ]

[ 504-63-2 ] Synthesis Path-Upstream   1~41

  • 1
  • [ 95-51-2 ]
  • [ 504-63-2 ]
  • [ 611-33-6 ]
YieldReaction ConditionsOperation in experiment
57% at 150℃; for 8 h; Inert atmosphere; Sealed tube General procedure: An ampule was charged with 0.02 mmol of FeCl3·6H2O, 2 mmol of aniline, 4 mmol of carbon tetrachloride, and 8 mmol 1,3-propanediol under argon. The sealed ampule was placed into a pressure reactor, which was hermetically closed and heated at 150°C for 8 h with continuous stirring. After the reaction completion, the reactor was cooled to room temperature, the ampule was opened, the reaction mixture was poured in hydrochloric acid. The aqueous layer was separated, neutralized with 10percent sodium hydroxide solution, and extracted with methylenechloride. The organic layer was filtered, the solvent was distilled off, and the residue was distilled in a vacuum. Physicochemical characteristics and spectral data of the obtained compounds 2a–2l corresponded to the literature data.
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
[3] Journal of Organic Chemistry, 1987, vol. 52, # 9, p. 1673 - 1680
  • 2
  • [ 123-75-1 ]
  • [ 504-63-2 ]
  • [ 19748-66-4 ]
  • [ 1012-29-9 ]
Reference: [1] Journal of Organometallic Chemistry, 1989, vol. 373, p. 343 - 352
  • 3
  • [ 108-44-1 ]
  • [ 504-63-2 ]
  • [ 612-60-2 ]
  • [ 7661-55-4 ]
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
  • 4
  • [ 108-44-1 ]
  • [ 504-63-2 ]
  • [ 612-60-2 ]
  • [ 7661-55-4 ]
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
  • 5
  • [ 108-42-9 ]
  • [ 504-63-2 ]
  • [ 612-61-3 ]
  • [ 635-27-8 ]
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
  • 6
  • [ 108-42-9 ]
  • [ 504-63-2 ]
  • [ 612-61-3 ]
  • [ 31084-60-3 ]
Reference: [1] Organometallics, 2016, vol. 35, # 11, p. 1973 - 1977
  • 7
  • [ 108-42-9 ]
  • [ 504-63-2 ]
  • [ 612-61-3 ]
  • [ 635-27-8 ]
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
  • 8
  • [ 62-53-3 ]
  • [ 504-63-2 ]
  • [ 479-59-4 ]
YieldReaction ConditionsOperation in experiment
73% With IrCl3·3H3O; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,3,5-trimethyl-benzene at 165℃; for 18 h; General procedure: To a vial was added aniline (1.0 mmol), IrCl3·3H3O (5.0 molpercent based on 1,3-propanediol),rac-BINAP (7.5 molpercent) under air. To the vial was added mesitylene (0.5 mL) then1,3-propanediol (1.3 mmol) was added and stirred at 165 °C for 18 h. After the reaction, the resulting mixture was diluted with hexane. Then, the mixture was filtrated by filter paper, and was concentrated in vacuo. The resulting residue was purified by flash column chromatography on SiO2 (tBuOMe:Hexane=1:15) to yield 2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine.
Reference: [1] Synlett, 2018, vol. 29, # 18, p. 2385 - 2389
  • 9
  • [ 635-46-1 ]
  • [ 504-63-2 ]
  • [ 479-59-4 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 7, p. 1090 - 1096
  • 10
  • [ 635-46-1 ]
  • [ 504-63-2 ]
  • [ 479-59-4 ]
  • [ 6613-29-2 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 7, p. 1090 - 1096
  • 11
  • [ 94-09-7 ]
  • [ 504-63-2 ]
  • [ 73987-38-9 ]
YieldReaction ConditionsOperation in experiment
45% at 150℃; for 12 h; Green chemistry Accurately weigh 0.005mmol (l. Lmg) of the transition metal, add 10mL has been put into the magnetic stirrer Young's reaction tube, The oxygen reaction was carried out in the Young's reaction tube, and the reaction was carried out under oxygen conditions. The syringe was applied to the Young's reaction tubeA solution of 0.04 mmol of co-catalyst I, 0.08 mmol of co-catalyst II, 0.2 mmol of 4-carboxylate and 1 ml of l-3'-propylene glycol, the above-mentioned Young's reaction tube was placed on a magnetic stirrer and stirred at 150 ° C for 12 h. After the reaction was completed,The pH of the solution was neutral, and the reaction solution was post-treated to obtain pure product of ethyl 6-formate quinoline in a yield of 45percent.
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 3284 - 3290
[2] Patent: CN106543078, 2017, A, . Location in patent: Paragraph 0113; 0114
  • 12
  • [ 53472-18-7 ]
  • [ 504-63-2 ]
  • [ 40000-20-2 ]
Reference: [1] Patent: CN108530443, 2018, A, . Location in patent: Paragraph 0058; 0060-0062
  • 13
  • [ 504-63-2 ]
  • [ 627-30-5 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1728 - 1733[2] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 10, p. 2032 - 2038
[3] Journal of the American Chemical Society, 1916, vol. 38, p. 2481
[4] Bulletin de la Societe Chimique de France, 1940, vol. <5>7, p. 257
[5] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1941, vol. 212, p. 643
[6] Journal of the American Chemical Society, 1941, vol. 63, p. 1733,1736
[7] Journal of the American Chemical Society, 1921, vol. 43, p. 369
[8] Journal of the American Chemical Society, 1920, vol. 42, p. 2096
[9] Journal of the Chemical Society, 1928, p. 2443
[10] Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1927, vol. 130, p. 163
[11] Chemische Berichte, 1921, vol. 54, p. 3119
[12] Org.Synth.Coll.Vol.I<1932>,S.519;deutsche Ausgabe,S.535,
[13] J. Gen. Chem. USSR (Engl. Transl.), 1966, vol. 36, p. 1629 - 1632[14] Zhurnal Obshchei Khimii, 1966, vol. 36, p. 1628 - 1633
  • 14
  • [ 56-81-5 ]
  • [ 504-63-2 ]
  • [ 142-28-9 ]
  • [ 627-30-5 ]
Reference: [1] Patent: WO2009/773, 2008, A1, . Location in patent: Page/Page column 18-19
  • 15
  • [ 504-63-2 ]
  • [ 142-28-9 ]
  • [ 627-30-5 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 16, p. 3361 - 3364
[2] Annales de Chimie (Cachan, France), 1878, vol. <5>14, p. 477;[3] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1881, p. 408
[4] Annales de Chimie (Cachan, France), 1878, vol. <5>14, p. 477;[5] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1881, p. 408
[6] Journal of Organic Chemistry, 1983, vol. 48, # 17, p. 2825 - 2828
  • 16
  • [ 56-23-5 ]
  • [ 504-63-2 ]
  • [ 627-30-5 ]
Reference: [1] Russian Journal of Organic Chemistry, 2006, vol. 42, # 11, p. 1615 - 1621
  • 17
  • [ 504-63-2 ]
  • [ 2396-61-4 ]
  • [ 627-30-5 ]
Reference: [1] Chemische Berichte, 1921, vol. 54, p. 3119
  • 18
  • [ 7647-01-0 ]
  • [ 504-63-2 ]
  • [ 2396-61-4 ]
  • [ 142-28-9 ]
  • [ 627-30-5 ]
Reference: [1] Chemische Berichte, 1921, vol. 54, p. 3119
  • 19
  • [ 504-63-2 ]
  • [ 4176-55-0 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 4, p. 701 - 707
[2] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 11, p. 3160 - 3166
[3] Journal of the American Chemical Society, 1956, vol. 78, p. 454,457
[4] Proceedings of the Imperial Academy (Tokyo), vol. 2, p. 545[5] Chem. Zentralbl., 1927, vol. 98, # I, p. 2415
[6] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 2, p. 113 - 116
[7] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 2, p. 500 - 509
  • 20
  • [ 504-63-2 ]
  • [ 4176-55-0 ]
  • [ 462-39-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 4, p. 861 - 866
  • 21
  • [ 504-63-2 ]
  • [ 4176-55-0 ]
  • [ 462-43-1 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 8, p. 1473 - 1477[2] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1633 - 1638
[3] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 8, p. 1473 - 1477[4] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1633 - 1638
  • 22
  • [ 504-63-2 ]
  • [ 627-31-6 ]
Reference: [1] Journal of the Chemical Society, 1948, p. 642[2] Journal of the Chemical Society, 1934, p. 339
[3] Monatshefte fuer Chemie, 1881, vol. 2, p. 638
[4] Journal of the American Chemical Society, 1924, vol. 46, p. 765
[5] Angewandte Chemie, 1972, vol. 84, p. 158 - 160
[6] Tetrahedron Letters, 1979, p. 1801 - 1804
  • 23
  • [ 504-63-2 ]
  • [ 627-31-6 ]
  • [ 627-32-7 ]
Reference: [1] Synthetic Communications, 1983, vol. 13, # 5, p. 387 - 392
  • 24
  • [ 50-00-0 ]
  • [ 107-02-8 ]
  • [ 4704-94-3 ]
  • [ 504-63-2 ]
Reference: [1] Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
  • 25
  • [ 50-00-0 ]
  • [ 75-07-0 ]
  • [ 115-77-5 ]
  • [ 2163-42-0 ]
  • [ 4704-94-3 ]
  • [ 504-63-2 ]
Reference: [1] Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
[2] Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
  • 26
  • [ 50-00-0 ]
  • [ 75-07-0 ]
  • [ 68516-39-2 ]
  • [ 115-77-5 ]
  • [ 4704-94-3 ]
  • [ 2831-90-5 ]
  • [ 68658-38-8 ]
  • [ 504-63-2 ]
Reference: [1] Liebigs Annalen der Chemie, 1985, # 5, p. 1082 - 1087
  • 27
  • [ 105-53-3 ]
  • [ 71-23-8 ]
  • [ 623-72-3 ]
  • [ 105-37-3 ]
  • [ 504-63-2 ]
Reference: [1] Chinese Journal of Catalysis, 2016, vol. 37, # 4, p. 484 - 493
  • 28
  • [ 506-96-7 ]
  • [ 504-63-2 ]
  • [ 592-33-6 ]
Reference: [1] Journal of the American Chemical Society, 1924, vol. 46, p. 765
[2] Journal of Organic Chemistry, 1968, vol. 33, # 5, p. 2013 - 2020
[3] Journal of the American Chemical Society, 1934, vol. 56, p. 1398,1399
  • 29
  • [ 112-82-3 ]
  • [ 504-63-2 ]
  • [ 23377-40-4 ]
YieldReaction ConditionsOperation in experiment
88.4% With potassium hydroxide In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 16 h; In a 1000ml round bottom flask,Add n-hexadecyl bromide (2) 97.5 g (0.32 mol, 1 eq), 1,3-propanediol (3) 73.5 g (0.96 mol, 3 eq),DMSO 200ml,DMF 200ml andPotassium hydroxide 72g (1.28mol, 4eq), stirred at room temperature16h.After completion of the reaction, 500 ml of water was added to the reaction solution, then the pH was adjusted to neutrality with a 5M hydrochloric acid solution, and the mixture was extracted with ethyl acetate (500 ml×2). The organic layers were combined and the organic layer was washed with saturated brine (500 ml×2). ), collecting organic phase,Dry with 10 g of anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain 102 g of a yellow solid.Recrystallization of petroleum ether yielded 85 g of white flake-like crystals with a yield of 88.4percent.
77%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; oil at 0 - 20℃; for 0.166667 h;
Stage #2: With potassium iodide In N,N-dimethyl-formamide; oil at 95℃; for 4 h;
General procedure: To a solution of 1,3-propanediol (19) (6.51 mL, 90 mmol) in dry DMF (40 mL) was added NaH (60percent oil dispersion; 1.20 g, 30 mmol) in installments at 0 °C and the mixture was stirred at room temperature for 10 min. Dodecyl bromide (4.80 mL, 20 mmol) and KI (3.32 g, 20 mmol) were added and the mixture was heated at 95 °C for 4 h. After cooling, the mixture was poured into ice-water and extracted with AcOEt. The extracts were washed with brine, dried over Na2SO4 and evaporated. The resulting residue was purified by flash CC (silica gel; AcOEt/hexane, 1:2) to provide dodecyl ether 20a (3.38 g, 69percent). Tetradecyl ether 20b (79percent) and hexadecyl ether 20c (77percent) were similarly prepared from 1,3-propanediol (19).
Reference: [1] Patent: CN107936059, 2018, A, . Location in patent: Paragraph 0011; 0029; 0030
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3658 - 3665
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 12, p. 2887 - 2893
[4] Chemistry and Physics of Lipids, 1996, vol. 83, # 1, p. 77 - 85
[5] Molecular Therapy - Nucleic Acids, 2017, vol. 8, p. 158 - 168
  • 30
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  • [ 504-63-2 ]
  • [ 23377-40-4 ]
Reference: [1] ChemMedChem, 2013, vol. 8, # 3, p. 511 - 520
  • 31
  • [ 20779-14-0 ]
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  • [ 23377-40-4 ]
Reference: [1] Patent: US2012/58976, 2012, A1, . Location in patent: Page/Page column 18
  • 32
  • [ 109-64-8 ]
  • [ 105-53-3 ]
  • [ 503-30-0 ]
  • [ 3779-29-1 ]
  • [ 504-63-2 ]
Reference: [1] Chemistry Letters, 1987, p. 2235 - 2238
  • 33
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  • [ 504-63-2 ]
  • [ 73842-99-6 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydride In tetrahydrofuran The synthesis of an exemplary "bottom fragment" 15 for making dictyostatin and analogs is shown in Figure 1.1,3-Propanediol 3 was elaborated via Evans chiral auxiliary-based methods to the known, bis-TBS-protected Homer-Wadsworth-Emmons product 10 in nine steps. See, Phukan, P. ; Sasmal, S. ; Maier, M. E. Eur. J. Org. Chem. 2003, 1733, and Andrus, M. B. ; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049.
99%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil for 0.916667 h; Inert atmosphere
Stage #2: at 20℃; for 0.833333 h; Inert atmosphere
To a dried 250 mL RBF under an atmosphere of argon at room temperature was added 1 00 mL of distilled THF and 2.1 g of sodium hydride (60percent dispersion in mineral oil; Aldrich). The mixture was stirred vigorously and 1 ,3-propanediol (4.0 g, 50 mmol; Aldrich) was added over 1 0 minutes via syringe. The reaction was allowed to stir for 45 minutes before tert-butyldimethylsilyl chloride (7.9 g, 52.7 mmol; Aldrich) was added portion wise over 5 minutes. The reaction was then allowed to stir for a further 45 minutes at room temperature before being quenched slowly with 20 mL of 10percent aqueous sodium carbonate solution. This mixture was then transferred to a separatory funnel. After being vigorously shaken, the biphasic mixture was separated and the aqueous phase was further extracted with two 50 mL portions of ether. The combined organic phases are then dried with sodium sulfate and filtered through a plug of 1 inch of Celite and 1 inch of flash silica (silica gel 60, EMD) via a 100 mL sinter funnel under vacuum into a 500 mL RBF, with the sodium sulfate residue washed with a further 50 mL of ether. The collected solution was then reduced under vacuum on a Buchi rotary evaporator to give compound L, as a light yellow oil in 99percent yield and >95percent purity
99%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.916667 h; Inert atmosphere
Stage #2: at 20℃; for 0.833333 h; Inert atmosphere
Synthesis of Intermediate L Compound L was prepared according to the procedure of McDougal, P. G.; Rico, J. G.; Oh, Y.-L; Condon, B. J. Org. Chem., 1986, 51, 3388-3390. To a dried 250 mL RBF under an atmosphere of argon at room temperature was added 100 mL of distilled THF and 2.1 g of sodium hydride (60percent dispersion in mineral oil; Aldrich). The mixture was stirred vigorously and 1,3-propanediol (4.0 g, 50 mmol; Aldrich) was added over 10 minutes via syringe. The reaction was allowed to stir for 45 minutes before tert-butyldimethylsilyl chloride (7.9 g, 52.7 mmol; Aldrich) was added portion wise over 5 minutes. The reaction was then allowed to stir for a further 45 minutes at room temperature before being quenched slowly with 20 mL of 10percent aqueous sodium carbonate solution. This mixture was then transferred to a separatory funnel. After being vigorously shaken, the biphasic mixture was separated and the aqueous phase was further extracted with two 50 mL portions of ether. The combined organic phases are then dried with sodium sulfate and filtered through a plug of 1 inch of Celite and 1 inch of flash silica (silica gel 60, EMD) via a 100 mL sinter funnel under vacuum into a 500 mL RBF, with the sodium sulfate residue washed with a further 50 mL of ether. The collected solution was then reduced under vacuum on a Buchi rotary evaporator to give compound L, as a light yellow oil in 99percent yield and >95percent purity. The 1H NMR spectrum in CDCI3 agreed with the previously reported data. (See, McDougal, P. G.; Rico, J. G.; Oh, Y.-L; Condon, B. J. Org. Chem., 1986, 51, 3388-3390.)
98%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2 h; Inert atmosphere
Stage #2: at 20℃;
To a solution of 60 sodium hydride (2.1g, 60percent disp. in 61 mineral oil, 52.6mmol) in dry 48 THF (60mL), a solution of 62 propane-1,3-diol (3.9mL, 52.6mmol) in dry THF (20mL) was added under argon at 0°C. The reaction mixture was stirred for 120min at the same temperature, and then a solution of 63 tert-butyldimethylsilyl chloride (7.9g, 52.6mmol) in dry THF (20ml) was added dropwise. After stirring overnight, the reaction was quenched with satd aq NaHCO3 (50ml). The aqueous layer was washed with Et2O (3×20mL). The combined organic layers were washed with brine (30ml), dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give 9.81g (98percent) of alcohol 49 9 as a yellow oil, which was pure enough to be used for Mitsunobu reaction. 1H NMR (300MHz, CDCl3) δ 3.84–3.76 (m, 4H), 2.60 (s, 1H), 1.82–1.73 (m, 2H), 0.89 (s, 9H), 0.07 (s, 6H); 13C NMR (75MHz, CDCl3) δ 63.4, 62.8, 34.9, 26.5, 18.8, −4.9
90%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 2.5 h; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
Stage #3: With methanol; sodium hydrogencarbonate In tetrahydrofuran at 20℃; Inert atmosphere
To a solution of 1,3-propanediol (3 mL, 40 mmol) in THF (60 mL) was added NaH (1.2 g, 60percent, 20 mmol) at rt. After stirring for 2.5 h, TBSCl (630 mg, 4.3 mmol) was added and the mixture was stirred overnight before the addition of NaHCO3 solution in MeOH. The solution was then extracted with DCM, washed with water and brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography (30percent EtOAc in hexanes) to afford 2-((tert-butyldimethylsilyl)oxy)ethanol ether (800 mg, 90percent based on TBSCl) as a colorless oil. To a solution of this TBS ether (590 mg, 3.11 mmol) in DCM (29 mL) was added NaHCO3 and Dess-Martin periodinane at rt. After stirring for 30 min, the solution was concentrated, diluted with hexane to participate byproduct, filtered and concentrated carefully to give crude 2-((tert-butyldimethylsilyl)oxy)acetaldehyde. A solution of this crude aldehyde in t-BuOH (13 mL) and 2-methyl-2-butene (1.5 mL) was treated with a solution of NaClO2 (500 mg, 5.5 mmol) and NaH2PO4 (1.85 g, 15.4 mmol) in water (12 mL) dropwise. After stirring for 1 h, the reaction was partitioned between brine and DCM. The organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromatography (30percent EtOAc in hexanes) to afford acid 11 (431 mg, 68percent over 2 steps) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 3.91 (2H, t, J = 6.1 Hz), 2.58 (2H, t, J = 6.1 Hz), 0.89 (9H, s), 0.09 (6H, s).
90%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.75 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 12 h; Inert atmosphere
To a stirred solution of 1,3-propane diol 17 (3.0 g, 39.42 mmol) in dry THF (40 mL) at 0 °C was added oil free NaH (0.95 g, 39.42 mmol, 1.0 equiv) in portions over 15 min. The reaction mixture was stirred at room temperature for 30 min, then cooled to 0 °C after which TBDMSCl (5.94 g, 39.42 mmol, 1.0 equiv) was added. The reaction mixture was stirred at room temperature for 12 h. It was then quenched with ice cold water (10 mL) and the solution extracted with EtOAc (3 .x. 30 mL). The combined organic layers were washed with water, brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column chromatography using petroleum ether/EtOAc (9:1 to 4:1) as eluent to give 18 (6.75 g, 90percent) as a colorless oil. IR (CHCl3) ν = 3368, 2931, 2859, 1473, 1257, 1065, 985, 838, 774 cm-1. 1H NMR (400 MHz, CDCl3/TMS): δ = 0.033 (s, 6H), 0.86 (s, 9H), 1.71-1.74 (m, 2H), 2.93 (br s, 1H), 3.73 (t, J = 5.5 Hz, 2H), 3.78 (t, J = 5.5 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ = -5.4 (2C), 18.1, 25.7 (3C), 34.1, 62.4, 62.8.
71% With 1H-imidazole; dmap In dichloromethane at 25℃; for 18 h; Inert atmosphere General procedure: A mixture of (S)-3 (2.38 g, 13.52 mmol), imidazole (1.11 g, 16.38 mmol), TBSCl (2.26 g, 15.0 mmol) and DMAP (catalytic) in CH2Cl2 (30 mL) was magnetically stirred for 18 h. The mixture was poured into water (20 mL), and extracted with Et2O (3 * 10 mL). The ether layer was washed with water (2 * 10 mL) and brine (1 * 5 mL), and dried. Removal of the solvent followed by chromatography of the residue (silica gel, 0-10percent Et2O/hexane) afforded pure 5. Yield: 3.60 g (92percent).
63%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 1 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 12 h; Inert atmosphere
To a suspension of NaH (1.1 g, 27.3 mmol) in THF (40 mL) at RT was added 1,3-propanediol (2.28 g, 30 mmol) in THF (8 mL). The suspension was stirred for 1 h before being cooled to 0 °C. TBSCl (4.11 g, 27.3 mmol) in THF (10 mL) was added dropwise. The reaction mixture was allowed to warm to RT and was stirred for 12 h. The reaction was quenched by the addition of 10percent (w/w) aqueous K2CO3 (10 mL). The aqueous solution was concentrated in vacuo to remove the THF component and then was extracted with Et2O (100 mL). The combined organic extracts were washed with H2O (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by FC on silica gel (hexanes/EtOAc = 100:1-5:1) to afford the TBS ether 21 (3.27 g, 63percent) as a colorless oil
51% With triethylamine In hexane; acetonitrile at 20℃; for 24 h; Inert atmosphere General procedure: In a flame-dried100 mL round-bottom flask equipped with a teflon magnetic stir bar,diol(5.0 mmol) was added to acetonitrile (12.5 mL) and hexanes (37.5 mL).Triethylamine (Et3N, 0.84 mL, 6.00 mmol, 1.2 equiv) and tertbutyldimethylsilylchloride (TBSCl, 0.53 g, 5.0 mmol, 1.0 equiv) were addedto the solution and the resulting biphasic mixture was stirred vigorously atroom temperature for 24 h under a N2 atmosphere. The reaction was quenchedwith saturated aqueous ammonium chloride (NH4Cl, 50 mL), and extractedwith ethyl acetate (EtOAc, 3 50 mL). The combined organic phase waswashed with brine (3 50 mL) and dried over anhydrous sodium sulfate(Na2SO4). The crude product was purified by silica gel column chromatography(10–15percent EtOAc/hexanes).

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YieldReaction ConditionsOperation in experiment
82.4% at 20℃; for 1 h; 3.69 g (48.5 mmol) of 1,3-propanediol was added to the organic phase obtained in Example 1, and the mixture was stirred at room temperature for 1 hour. After separation of the separated aqueous phase, the solvent was distilled off with an evaporator. 2 ml of toluene and 120 ml of heptane were added to the remaining oily matter to precipitate crystals. The obtained crystals were washed with 30 ml of heptane and then dried, 7.44 g (yield: 82.4percent) of 1,3-propanediol ester (2- (1,3,2-dioxaborinan-2-yl) benzonitrile) of 2-cyanophenylboronic acid was obtained. The crystal contained 0.40percent of 1-phenyl-1- (2,2,6,6-tetramethylpiperidin-1-yl) methylimine
57.2% for 20 h; Step 1: Synthesis of 2-(1,3,2-dioxaborinan-2-yl)benzonitrile
49.0 g (334 mmol) 2-cyanobenzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol were dissolved in 1 L CH2Cl2 with stirring in a 2 L round bottom flask for 20 h. The solution was then poured over a filter with suction to remove gummy solids. The filtrate was then dried with anhydrous MgSO4 to remove residual water, filtered and evaporated of solvent to give light-colored oil. The oil was then dissolved in CH2Cl2 and purified on a silica gel plug using CH2Cl2 as eluent. The product fractions were evaporated down to give the product as clear oil (35.7 g, 57.2percent yield).
57.2% for 20 h; Step 1: synthesis of 2-(1,3,2-dioxaborainan-2-yl)benzonitrile 49.0 g (334 mmol) 2-cyano-benzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol and stirred while 2 ℓ 1 ℓ round bottom flask in CH2Cl2 20 hours dongan was dissolved. Then, the solution was poured into a suction filter to remove the solids on the gum. Then, the filtrate was dried over anhydrous MgSO4 and removal of the residue, filtered, to give a lighter colored oil by evaporation of the solvent. Thereafter, the oil was dissolved in CH2Cl2, was purified using CH2Cl2 as eluent on a silica gel plug. Distilling the product fractions to obtain the product (35.7 g, 57.2percent yield) as a clear oil
20% for 24 h; Reflux 2-cyano phenyl boronic acid and 1,3 propanediol was solubilized in anhydrous toluene. The reaction mixture was refluxed in a flask equipped with a Dean-Stark apparatus. After 24 h, the reaction was concentrated under reduced pressure to give colorless oil. The crude product was purified on silica gel (DCM) to give 2-[1-3]dioxaborinan-2-yl-benzonitrile; yield: 20percent; 1H NMR (300 MHz, CDCl3) δ ppm 2.08 (t, J = 5.4 Hz, 2H), 4.21 (q, J = 5.4 Hz, 4H), 5.31 (ls, 2H), 7.45 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.53 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H). The 2-[1-3]dioxaborinan-2-yl-benzonitrile was readily solubilized in toluene (0.2 M). To this solution, compound 3e (1eq), PdCl2(dppf) (2percent) and K3PO4 (2 eq) were added. The mixture was refluxed during 2 h, then was concentrated under reduced pressure. The obtained crude product was dissolved in ethyl acetate and washed by HCl 1N. The organic layer was concentrated under reduced pressure and purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (70/30) to give 9 as a yellow powder; purity 99percent; yield: 83percent; mp: 169-170 °C; 1H NMR (300 MHz, CDCl3) δ ppm 1.29 (t, J = 6.9 Hz, 3H), 2.10 (s, 3H), 4.23 (q, J = 6.9 Hz, 2H), 7.61 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.69 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.75 (d, J = 8.7 Hz, 2H), 7.82 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.82 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.82 (d, J = 8.7 Hz, 2H), 9.13 (s, 1H), 9.95 (sl, 1H); 13C NMR (75 MHz, CDCl3) δ ppm 15.0, 23.9, 60.8, 110.2, 110.9, 119.3, 119.5, 129.3, 130.1, 130.2, 132.7, 134.5, 134.8, 137.1, 139.6, 144.2, 148.4, 162.7, 169.6; LCMS (EI (+)) m/z = 389 [M + H] +. HRMS (EI) calcd for C21H18N4O2 [M + H]+ 375.14517. Found 375.14454.

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