Water → HCID 178448132、化合物

HRID 2214328

反応式

HRID 2214328 の反応式
[C:1]1([C@H:7]([CH3:18])[CH2:8]C2C=CC(C(Cl)=O)=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([CH2:33][CH2:34][CH3:35])[CH2:29][CH2:28]1.N1C=CC=CC=1.[OH2:42]>>[CH2:33]([C@H:30]1[CH2:31][CH2:32][C@H:27]([O:26][C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:18])=[O:42])[CH2:28][CH2:29]1)[CH2:34][CH3:35]

参加物

6

反応物 5

HCID 962WaterHCID 1049PyridineHCID 1140TolueneHCID 86591923(R)-4-(2-phenylpropyl)benzoyl chlorideHCID 178448131HCID 178448131、化合物

生成物 1

HCID 178448132HCID 178448132、化合物収率 75%

実験手順

Into a 200 mL eggplant-type flask, 20.0 g (83.2 mmol) of (R)-4-(2-phenylpropyl)benzoic acid obtained in third step, 80 mL of tetrachloroethylene and 19.8 g (166 mmol) of thionyl chloride were added, followed by stirring at 70° C. for 3 hours, and excess of thionyl chloride and tetrachloroethylene were distilled off under reduced pressure to obtain 22.0 g of (R)-4-(2-phenylpropyl)benzoyl chloride [H-Ph-CH(CH3)—CH2-Ph-COCl]. Then, to a 200 mL four-necked flask, 22.0 g of (R)-4-(2-phenylpropyl)benzoyl chloride, 103 mL of toluene, 11.8 g (83.2 mmol) of trans-1-hydroxy-4-propylcyclohexane and 7.90 g (99.9 mmol) of pyridine were added, followed by stirring at room temperature overnight. Water was added to the reaction solution to separate the organic phase, the aqueous phase was extracted with toluene, and the toluene layer and the organic phase were put together and washed with diluted hydrochloric acid, a sodium hydrogen carbonate aqueous solution and saturated salt solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a crude product. The crude product was purified by silica gel column chromatography (developing solvent: hexane/toluene=3/1), and recrystallization from ethanol was carried out to obtain 22.7 g (62.4 mmol) of (R)-1-[(trans-4-propylcyclohexyloxycarbonyl)phenyl]- 2-phenylpropane [H-Ph-CH(CH3)—CH2-Ph-C(O)O-Cy-C3H7] as white crystals (yield: 75%).

後処理

  1. customto separate the organic phase
  2. extractionthe aqueous phase was extracted with toluene
  3. washwashed with diluted hydrochloric acid
  4. dry with materiala sodium hydrogen carbonate aqueous solution and saturated salt solution and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customto obtain a crude product
  7. customThe crude product was purified by silica gel column chromatography (developing solvent: hexane/toluene=3/1), and recrystallization from ethanol

出典と根拠

ORDレコード
ord-576ed8583e1a4c4aa8e8af494a3bc026
出典データセット
uspto-grants-2006_09
特許番号
US07108895B2

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