4-Hydroxybenzaldehyde → HCID 58097238, 화합물

HRID 2092230노트

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HRID 2092230 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

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

후처리

  1. extractionthe mixture is extracted three times with in each case 500 ml of ethyl acetate
  2. washThe combined organic phases are washed in each case once with 500 ml water and 500 ml of sat. aqueous sodium chloride solution
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent is removed on a rotary evaporator
  5. customthe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: ethyl acetate/petroleum ether 1:9→2:8)

출처 및 근거

ORD 기록
ord-56b1055043594a15b4791c7dd93df15e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440700B2

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