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[ CAS No. 29668-44-8 ]

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Chemical Structure| 29668-44-8
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CAS No. :29668-44-8MDL No. :MFCD00010092
Formula : C9H8O3 Boiling Point : 221.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :164.16Pubchem ID :248127
Synonyms :

Computed Properties of [ 29668-44-8 ]

TPSA : 35.5 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.22 Rotatable Bond Count : 1

Safety of [ 29668-44-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29668-44-8 ]

  • Upstream synthesis route of [ 29668-44-8 ]
  • Downstream synthetic route of [ 29668-44-8 ]

[ 29668-44-8 ] Synthesis Path-Upstream   1~19

  • 1
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  • [ 10288-72-9 ]
YieldReaction ConditionsOperation in experiment
94% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 50℃; for 16 h; To a solution of 2,3-dihydro-benzo[1,4]dioxin-6-carboxaldehyde (30.0 g, 183 mmol) in 500 ml CH2Cl2 was added mCPBA (37.85 g, 219 mmol).
The suspension was heated to 50° C.
After 16 h saturated NaHCO3 was added and the mixture was extracted with CH2Cl2 The combined organics were concentrated in vacuo and taken up in MeOH and 200 ml 4M NaOH was added.
After 2 h the mixture was acidified with 4M HCl and extracted with ethyl acetate.
The combined organics were washed with saturated NaHCO3, washed with brine, concentrated in vacuo, and taken up in CH2Cl2.
The solution was filtered to remove the precipitate.
The resulting solution was stirred with saturated NaHCO3 for 1 h, separated, dried over MgSO4, filtered and concentrated in vacuo to give 2,3-dihydro-benzo[1,4]dioxin-6-ol (26.92 g, 94percent).
94%
Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 50℃; for 16 h;
Stage #2: With sodium hydroxide In methanol; water for 2 h;
To a solution of 2,3-dihydro-benzo[1,4]dioxin-6-carboxaldehyde (30.0 g, 183 mmol) in 500 ml CH2Cl2 was added mCPBA (37.85 g, 219 mmol).
The suspension was heated to 50° C.
After 16 h saturated NaHCO3 was added and the mixture was extracted with CH2Cl2.
The combined organics were concentrated in vacuo and taken up in MeOH and 200 ml 4M NaOH was added.
After 2 h the mixture was acidified with 4M HCl and extracted with ethyl acetate.
The combined organics were washed with saturated NaHCO3, washed with brine, concentrated in vacuo, and taken up in CH2Cl2.
The solution was filtered to remove the precipitate.
The resulting solution was stirred with saturated NaHCO3 for 1 h, separated, dried over MgSO4, filtered and concentrated in vacuo to give 2,3-dihydro-benzo[1,4]dioxin-6-ol (26.92 g, 94percent).
92% for 0.0833333 h; Procedure: 2,3-dihydrobenzo[b][1 ,4]dioxine-6-carbaldehyde (2 g, 12.2 mmol, 1 eq.) was placed in a mortar, mCPBA (4.5 g, 18.3 mmol, 1.5 eq.) was added and the solids were mixed with a pestle. The resulting paste left at room temperature for 5 min and then diluted with NaOH (10percent in H20). The solution was washed with Et20, adjusted to pH 7 with HCI (2 m) and extracted with DCM. After the combined organic layers were dried over Na2S04, the solvent was evaporated and the product was purified via flash chromatography (Si02, nHex/EtOAc/AcoH 79/20/1 ).Yield: 1.7 g, 1 1.2 mmol, 92percent (off white solid).TLC: PE/EtOAc/AcOH 74/25/11H NMR (CDCI3,200 MHz, ppm): δ 6.72 (dd, J = 8.6, 0.4 Hz, 1 H), 6.40 (dd, J = 2.9, 0.4 Hz, 1 H), 6.33 (dd, J = 8.6, 2.9 Hz, 1 H), 4.32 - 4.14 (m, 4H), 4.00 (s, 1 H).13C NMR (CDCI3, 50 Hz, ppm): δ 150.1 , 144.0, 137.7, 1 17.7, 108.5, 104.4, 64.7, 64.2.
78% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 40℃; for 12 h; Inert atmosphere To a solution of 21 (5 g, 30.48 mmol) in DCM (80 mL) was added mCPBA (9 g, 45.72 mmol) under N2 atmosphere, and the reaction mixture was stirred for 12 h at 40. The resulting reaction mixture was quenched by saturated NaHCO3 aqueous solution (50 ml) and extracted with CH2Cl2 (50 mL × 3). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was dissolved in MeOH (20 ml) and added NaOH (1.46 g, 36.58 mmol). After the mixture was stirred for 15 min, the reaction mixture was adjusted to PH 6-7 with HCl (4 N aqueous solution) and extracted with methyl tert-butyl ether (50 mL × 3). The combined organic layer was washed with saturated aqueous NaHCO3 solution (100 ml) and brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with ethyl acetate/petroleum ether (1:3-1:2) to afford the intermediate 22 (3.6 g, 78percent yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ 8.92 (s, 1H), 6.62 (d, J = 8.4 Hz, 1H), 6.25-6.21 (m, 2H), 4.19 – 4.14 (m, 2H), 4.14 – 4.08 (m, 2H). 13C NMR (101 MHz, DMSO-d6) δ 151.55 (s), 143.50 (s), 136.09 (s), 117.08 (s), 107.93 (s), 103.59 (s), 64.23 (s), 63.67 (s).
63%
Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 50℃; for 48 h;
Stage #2: at 20℃; for 2 h;
Stage #3: With hydrogenchloride; water In methanol
EXAMPLE 37 Scheme 37a[00319] Synthesis of N-(6-(6-(2,3-dihydrobenzo[λ] [1,4]dioxin-6-yloxy)pyrimidin-4- ylamino)pyridin-2-yl)acrylamide (1-95)Step lTo a stirred solution of 2,3-dmydrobenzo[6][1,4]dioxine-6-carbaldehyde (1 g, 6.09 mmol) in CH2Cl2 (16 mL) was added /w-CPBA (4.204 g, 24.36 mmol). The suspension was heated at 50 °C for 2 days, was cooled to it, was quenched with saturated NaHCO3 soln. and was extracted with CH2Cl2 (3x10 mL). The combined extract was concentrated under reduced pressure, and then was dissolved in MeOH containing NaOH. The solution was stirred at rt for 2 h, was acidified with HCl and was extracted with ethyl acetate (3x10 mL). The combined extract was washed with saturated NaHCO3 solution and brine, was dried over anhydrous Na2SO4, was filtered and was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and was filtered. The DCM solution was dried over anhydrous Na2SO4, was filtered and was concentrated under reduced pressure to give 2,3-dihydrobenzo[Z>][1,4]dioxin-6-ol (0.591 g, 63percent) as a reddish brown oily liquid.

Reference: [1] Patent: US2005/209260, 2005, A1, . Location in patent: Page/Page column 114
[2] Patent: US2007/49609, 2007, A1, . Location in patent: Page/Page column 102
[3] Patent: WO2018/134254, 2018, A1, . Location in patent: Page/Page column 68
[4] Chemistry and Biodiversity, 2010, vol. 7, # 4, p. 887 - 897
[5] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 2051 - 2066
[6] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 380 - 396
[7] Patent: WO2009/51822, 2009, A1, . Location in patent: Page/Page column 150
[8] Bioscience, Biotechnology, and Biochemistry, 1992, vol. 56, # 2.3.4., p. 630 - 635
[9] Tetrahedron, 2004, vol. 60, # 40, p. 8899 - 8912
[10] Patent: US2011/87027, 2011, A1, . Location in patent: Page/Page column 11-12
[11] Patent: WO2012/49555, 2012, A1, . Location in patent: Page/Page column 56-57
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  • [ 2879-20-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 105, p. 80 - 105
  • 3
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  • [ 4442-54-0 ]
YieldReaction ConditionsOperation in experiment
81% With urea hydrogen peroxide adduct; sodium hydroxide In methanol; water for 1.5 h; Reflux General procedure: Aqueous NaOH (1.6 mL of 6 M solution) was added to a stirred solution of the urea-hydrogen peroxide complex (1:1) (6 g, 63.4 mmol) and aldehyde 3a-f (4.28 mmol) in 20 mL of CH3OH at rt. The reaction mixture was stirred at reflux for 1 h followed by the addition of the urea-hydrogen peroxide complex (1.5 g, 15.85 mmol) and reflux for 30 min. The reaction mixture was brought to rt, and the pH was adjusted to 3 with 18percent aqueous HCl. The precipitate was filtered, washed with 2 50 mL of ice water, and dried to afford 4a-f (82-94percent yield) as an off-white solid. For 4e, the reaction mixture was brought to rt, and the pH was adjusted to 3 with 18percent aqueous HCl. Methanol was evaporated, then the reaction mixture was diluted by 30 ml of water and extracted by CHCl3. Organic solution was washed by water, evaporated, and dried.
15 g With potassium permanganate In water at 70 - 80℃; for 2.66667 h; 25 g of the product of Example 1,Adding 500 mL of water to raise the temperature to 70-80 DEG C,Then, 30 g of KMnO4 + 500 mL of an aqueous solution was prepared,Dropping into the above reaction solution, heating for 40 minutes and heating to reflux for 2 hours,The reaction was terminated by TLC, cooled to room temperature, alkalified by addition of 10percent aqueous KOH,Filter cake washed with water to neutral, the filtrate acidified with concentrated hydrochloric acid,A large amount of white solid was precipitated, and the filter cake was washed with water and dried to obtain 23 g of a white solid in 90percent yield.
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1578 - 1581
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 11, p. 1951 - 1964
[4] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 1, p. 71 - 85
[5] Patent: US5530028, 1996, A,
[6] Patent: CN105801556, 2016, A, . Location in patent: Paragraph 0006; 0015; 0016; 0017
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YieldReaction ConditionsOperation in experiment
97% With caesium carbonate In DMF (N,N-dimethyl-formamide) at 70℃; for 16 h; Example 42; - preparation of 5-f f2,3-dihydro-f .41-benzodioxin)-6-vimethvf)amino}-N- (2-r2-dimethvlamino )ethvll-1 H-benzordelisoguinolin-1,3(2H)-dione; The synthetic route of this compound proceeds in a series of steps schematically shown in attached figure 2 and is described in more details as follows; a); in a first step, 500 mg 3,4-dihydroxybenzaldehyde, 2.6 g cesium carbonate (2 equivalents), 1.4 g 1,2-dibromoethane (2 equivalents) and 5 mL anhy-drous DMF were stirred at 70°C for 16 hours. After cooling, the solvent was evaporated under reduced pressure and the residue was submitted to a flash chromatography (Si02, eluent : CH2CI2), thus resulting in 575.3 mg (yield : 97 percent) of the intermediate shown as product A in figure 2 ;
86% With potassium carbonate In acetone at 60℃; for 36 h; Inert atmosphere To a solution of 3,4-dihydroxybenzaldehyde (20, 10 g, 72.40 mmol) in acetone (100 mL) was added K2CO3 (20 g, 144.92 mmol), then 1,2-dibromoethane (19 g, 101.44 mmol) was added dropwise under N2 atmosphere. The mixture was stirred for 36 h at 60. The resulting reaction mixture was cooled to room temperature and filtered, the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with ethyl acetate/petroleum ether (1:4, v/v) to provide the intermediate (21, 10.5 g, 86percent yield) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.80 (s, 1H), 7.43 (dd, J = 8.3, 1.9 Hz, 1H), 7.37 (d, J = 1.9 Hz, 1H), 7.05 (d, J = 8.3 Hz, 1H), 4.36-4.34 (m, 2H), 4.31-4.29 (m 2H). 13C NMR (101 MHz, DMSO-d6) δ 191.26 (s), 149.04 (s), 143.73 (s), 130.24 (s), 123.68 (s), 117.78 (s), 117.70 (s), 64.59 (s), 63.89 (s).
74% With potassium carbonate In N,N-dimethyl-formamide at 60 - 90℃; for 8 h; 138 mg of 3,4-dihydroxybenzaldehyde was dissolved in 5 ml of N,N-dimethylformamide.Add 100 mg of 1,2-dibromoethane and 300 mg of potassium carbonate,60-90°C reaction for 8 hours. After the reaction is over, the system is quenched with water.Extract three times with 30 ml of ethyl acetate and wash with saturated saline.Dry over anhydrous magnesium sulfate, filter, and concentrate to obtain intermediate 120 mg1,4-benzodioxane-7-carbaldehyde, yield 74percent, untreated,Used directly for the next reaction.
73% With potassium carbonate In acetone at 50 - 60℃; Industry scale SYNTHETIC PREPARATION 5
Synthesis of 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde Compound of formula (11)
A 2000 L reactor was charged with acetone (404.5 kg), followed by potassium carbonate (256 kg, 1852 mol) and 1,2-dibromoethane (241.5 kg, 1298 mol).
The mixture was heated at reflux.
A 500 L reactor was charged with acetone (606 kg) and 3,4-dihydroxybenzalhdehyde (128 kg, 926 mol).
The contents of the 500 L reactor were added to the 2000 L reactor at a rate of 150-180 kg/h while the reaction temperature was maintained at 50-60° C.
The reaction mixture was stirred at 54-60° C. for 12 h, was cooled to 20° C. and was filtered through a 500 L Nutsche filter.
The filter cake was washed with acetone (2*202 kg).
The filtrate and acetone washes were combined in a 2000 L reactor and the resultant solution was concentrated to dryness under reduced pressure at a temperature <40° C.
To the residue was added ethyl acetate (683 kg) and the resultant solution was washed with a 5percent by weight aqueous solution of potassium carbonate (256 kg).
The mixture was stirred for 0.5 h, allowed to settle for 0.5 h and the aqueous phase was removed.
This washing procedure was repeated three times in total.
The organic phase was temporarily set aside into drums.
A 2000 L reactor was charged with the combined aqueous washes, followed by ethyl acetate (113.9 kg).
The mixture was stirred for 0.5 h, allowed to settle for 0.5 h and the aqueous phase was removed.
The organic phase from the drums was added to the reactor followed by a 28percent by weight aqueous solution of sodium chloride (192 kg).
The mixture was stirred for 0.5 h, allowed to settle for 0.5 h and the aqueous phase was removed.
The organic phase was concentrated under reduced pressure at a temperature <45° C. until the mixture's ethyl acetate content was below 10percent (as determined by gas chromatography).
Petroleum ether (268.8 kg) was added to the residue at a rate of 80-90 kg/h while the mixture was maintained at a temperature of 35-45° C.
The mixture was cooled to 5° C. over 3 h and held at this temperature for a further 1 h, during which time a precipitate was deposited.
The resultant slurry was filtered through a centrifugal filter and dried to afford 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde (111.4 kg, 73percent) as an off-white solid: purity (HPLC-UV at 230 nm) 99.3percent.
67% With potassium carbonate In acetone for 25 h; Reflux Anhydrous potassium carbonate (21 g) was added in portions to a stirred solution of 27.6 g of 3,4-dihydroxy benzaldehyde in 100 ml of dry acetone followed by the dropwise addition of 4.3 ml of ethylene dibromide. Another 21 g of potassium carbonate and 4.3 ml of ethylene dibromide were added similarly and this was repeated twice more using a total of 84 g of potassium carbonate and 17.2 g of ethylene dibromide. Stirring and refluxing was continued for another 25 h. The reaction mixture was then filtered by sintered glass funnel and the solid residue was washed several times with acetone. The combined filtrate was concentrated to about 25 ml and the residue was poured onto crushed ice, asolid was separated which was filtered, dried and crystallized with methanol to give a low melting solid; mp 35-37 °C; 67percent yield; 1H NMR (300 MHz, DMSOd6): δ 4.30 (2H, d, J = 8.7 Hz, CH2-2), 4.33 (2H, d, J = 8.7, CH2-3), 7.03 (1H, d,J = 8.4 Hz, ArH-8), 7.36 (1H, d, J = 2.5 Hz, ArH-5), 7.43 (1H, dd, J = 8.4, 2.5 Hz, ArH-7), 9.79 (1H, s, Ar-CHO).
63% With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; General procedure: 43.80 g potassium carbonate (0.32 mol) and 15.1 cm3 1,2-dibromoethane (32.90 g, 0.18 mol) were added to a solutionof 22.00 g 13 (0.16 mol) or 26.70 g 15 (0.16 mol) in250 cm3 DMF. The reaction mixture was stirred at100–110 C for 4–8 h. After cooling to rt, the precipitatedinorganic salts were filtered and the reaction mixture wasevaporated to 80 cm3 in vacuo. The residue was pouredinto 670 cm3 water. The product was isolated as specified.2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde (16) Theaqueous phase was extracted with ethyl acetate(4 9 200 cm3), and the combined organic layer waswashed with brine and dried over Na2SO4. The crudeproduct was purified by distillation in vacuo to afford 16.Yield: 63percent; white solid; m.p.: 48–49 C (Ref. [63] 49.5–50.5 C); b.p.: 105–108 C (0.3 mbar); 1H NMR(300 MHz, CDCl3): d = 9.82 (s, 1H, CHO), 7.42–7.38 (m,2H, 5-HAr and 7-HAr), 6.98 (d, J = 8.7 Hz, 1H, 8-HAr),4.35–4.28 (m, 4H, OCH2CH2O) ppm; 13C NMR (75 MHz,CDCl3): d = 64.0 (OCH2CH2O), 64.7 (OCH2CH2O), 117.8(5-CAr or 8-CAr), 118.4 (5-CAr or 8-CAr), 124.2 (7-CAr),130.7 (6-CAr), 143.9 (4a-CAr), 149.1 (8a-CAr), 190.7(CHO) ppm; IR (KBr): m = 3001, 2883, 1687, 1581, 1506,1458, 1394, 1291, 1156, 1062, 887, 777 cm-1.
25 g With tetrabutylammomium bromide; sodium hydroxide In water for 5 h; Reflux In this step, 3,4-dihydroxybenzaldehyde was used as a starting material,And 1,2-dibromoethane in the alkaline environment for the reduction reaction, the synthesis of intermediate 2,3-dihydro-1,4-benzodioxane-6-carbaldehyde. The base used in the present reaction includes: potassium hydroxide, The condensing agent is an ammonium bromide compound such as tetrabutylammonium bromide; The molar ratio used was 3,4-dihydroxybenzaldehyde: 1,2-dibromoethane = 1: 5; The use of sodium hydroxide in excess of 5 times, under strong alkaline conditions for testing. The temperature used was the reflux temperature.

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  • [ 39270-39-8 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With sodium tetrahydroborate In ethanol at 0 - 20℃; for 1 h;
Stage #2: With water In ethanol
2,3-Dihydro-benzo [1, 4] dioxine-6-carbaldehyde [RN 29668-44-8] (3.04g, 18. 54mmol) was dissolved in ethanol (lOOmL) and cooled to 0°C. To the resulting solution was added sodium borohydride (1. 41g, 37. 07mmol). The resulting slurry was stirred at room temperature for 1 hour and then quenched with water (lOmL) before being concentrated to dryness under reduced pressure. The residue was partitioned between a 5percent aqueous solution of sodium hydrogen carbonate (20mL) and dichloromethane (2x50mL). The organic phases were combined and dried over magnesium sulfate then evaporated under reduced pressure to provide and oil which was purified on silica gel using a dichloromethane and methanol solvent gradient. This provided the desired product as a colourless oil (3. 00g, 97percent).
95% at 0℃; for 0.5 h; (2,3-Dihydrobenzo[b][l,4]dioxin-6-yl)methanol. To a solution of 2,3- dihydrobenzo[b][l,4]dioxine-6-carbaldehyde (TCI America Laboratory Chemicals B2019) (20 g, 0.12 mol) in MeOH (400 mL) at 0 0C was added NaBH4 (14 g, 0.36 mol) in portions. After stirring at 0 0C for 30 minutes, the mixture was neutralized to pH = 7 by addition of 2 M aqueous HCl. The MeOH was removed under reduced pressure, and the residue was extracted with DCM (2 x 200 mL). The combined organic layers were concentrated under reduced pressure to afford (2,3-dihydrobenzo[b][l,4]dioxin-6- yl)methanol (19 g, 95 percent).
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[2] Patent: WO2010/83246, 2010, A1, . Location in patent: Page/Page column 149-150
[3] Australian Journal of Chemistry, 1984, vol. 37, # 4, p. 893 - 901
[4] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 83, p. 11805 - 11808
[5] Tetrahedron, 2001, vol. 57, # 39, p. 8297 - 8303
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[7] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 125 - 136
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5971 - 5975
[9] Molecules, 2013, vol. 18, # 4, p. 3872 - 3893
[10] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5626 - 5632
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[2] Patent: US2010/298351, 2010, A1, . Location in patent: Page/Page column 34
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  • [ 31127-39-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 80℃; for 4 h; Inert atmosphere General procedure: To a suspension of aldehyde (30/35 mmol) in ethanol (50 mL) was added NH2OH*HCl (2 eq) and NaOH pellets (1.8 eq). The suspension was stirred at 80 C for 4 h and concentrated in vacuo. The crude product was extracted in EtOAc (200 mL). The organic layer was washed with 1 N HCl (2 200 mL), water (4 200 mL), dried (MgSO4) and concentrated in vacuo. If TLC showed impurities, the solid was washed with a minimum of cold Et2O to afford the aldoxime as a white powder.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 444 - 454
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1795 - 1799
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 15, p. 3965 - 3970
[4] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 4227 - 4230
[5] Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 977 - 981
[6] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5440 - 5448
[7] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2674 - 2677
[8] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 23-24, p. 3741 - 3747
  • 19
  • [ 29668-44-8 ]
  • [ 491833-29-5 ]
Reference: [1] Patent: CN106967042, 2017, A,
[2] Patent: CN106967042, 2017, A,
[3] Synthetic Communications, 2018, vol. 48, # 5, p. 594 - 600
[4] Synthetic Communications, 2018, vol. 48, # 5, p. 594 - 600
[5] Synthetic Communications, 2018, vol. 48, # 5, p. 594 - 600
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