4-Hydroxybenzaldehyde → HCID 58097238、化合物

HRID 1913492ノート

反応式

HRID 1913492 の反応式
[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

参加物

6

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 178521079HCID 178521079、化合物

生成物 1

HCID 58097238HCID 58097238、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

31.2 g (255.4 mmol) of 4-hydroxybenzaldehyde were 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 were added at RT. The mixture was stirred at 160° C. for 16 h. 4000 ml of water were then added, and the mixture was extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases were washed in each case once 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 (mobile phase gradient: ethyl acetate/petroleum ether 1:9→2:8).

後処理

  1. extractionthe mixture was extracted three times with in each case 500 ml of ethyl acetate
  2. washThe combined organic phases were washed in each case once 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 (mobile phase gradient: ethyl acetate/petroleum ether 1:9→2:8)

出典と根拠

ORDレコード
ord-024d762e3b39433abee8b46557289a93
出典データセット
uspto-grants-2013_12
特許番号
US08609686B2

反応ノート

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