4-Hydroxybenzaldehyde → HCID 58097238, 화합물

HRID 403013노트

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HRID 403013 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2-:16][C:17]([CH3:19])=[O:18].Cl[CH2:21][C@@H:22]([OH:25])[CH2:23]O.O>CN(C=O)C>[CH3:16][C:17]1([CH3:19])[O:25][C@H:22]([CH2:23][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:21][O:18]1

참가 물질

6

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 178521079HCID 178521079, 화합물

생성물 1

HCID 58097238HCID 58097238, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
160 °C

실험 절차

An amount of 31.2 g (255.4 mmol) of 4-hydroxybenzaldehyde was introduced in 400 ml of dry DMF and admixed at RT with 105.7 g (766.1 mmol) of potassium carbonate and also 50.0 g (332.0 mmol) of (S)-(−)-3-chloro-1,2-propanediol acetonide. The batch was stirred at 160° C. for 16 hours. The batch was then admixed with 4000 ml of water and extracted with three times 500 ml of ethyl acetate. The combined organic phases were washed once each with 500 ml of water and 500 ml of saturated aqueous sodium chloride solution. After drying over magnesium sulfate, the solvent was removed on a rotary evaporator and the residue was purified by column chromatography on silica gel 60 (eluent gradient: ethyl acetate/petroleum ether 1:9→2:8).

후처리

  1. extractionextracted with three times 500 ml of ethyl acetate
  2. washThe combined organic phases were washed once each with 500 ml of water and 500 ml of saturated aqueous sodium chloride solution
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was removed on a rotary evaporator
  5. customthe residue was purified by column chromatography on silica gel 60 (eluent gradient: ethyl acetate/petroleum ether 1:9→2:8)

출처 및 근거

ORD 기록
ord-1108c9725b7c43dab7c405ed6eed5949
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741834B2

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