Water → 14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol

HRID 486863

반응식

HRID 486863 반응식
C([O:3][C:4](=O)[C:5]([CH:22]([CH3:24])[CH3:23])=[CH:6][CH:7]=[C:8]([CH3:21])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:20])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:19])[CH2:17][Cl:18])C.[H-].C([Al+]C(C)C)(C)C.O>C1(C)C=CC=CC=1>[Cl:18][CH2:17][C:16]([CH3:19])=[CH:15][CH2:14][CH2:13][C:12]([CH3:20])=[CH:11][CH2:10][CH2:9][C:8]([CH3:21])=[CH:7][CH:6]=[C:5]([CH:22]([CH3:23])[CH3:24])[CH2:4][OH:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 21896610Diisopropylaluminium hydrideHCID 54546229Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate

생성물 1

HCID 5368470314-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol수율 83.7%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8, 12-tetradecatetraenoic acid ethyl ester (670 mg, 1.81 mmol) is dissolved in dry toluene (200 ml) under argon atmosphere and to the solution is gradually added a 1 M solution of diisopropylaluminum hydride in toluene (4 ml) while cooling and stirring on ethanol-dry ice bath. After 30 minutes, disappearance of the starting compound is confirmed. To the mixture is added water (1.5 ml), and after removing the bath, the mixture is thoroughly stirred. To the mixture is added a drying agent (anhydrous magnesium sulfate) and the mixture is further stirred. The mixture is filtered and concentrated and the resulting residue is chromatographed (n-hexane/ethyl acetate=12:1) on silica gel column to give the desired alcohol, 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraene-1-ol (492 mg, 79%) from the desired fraction.

후처리

  1. temperaturewhile cooling
  2. customafter removing the bath
  3. stirringthe mixture is thoroughly stirred
  4. additionTo the mixture is added a drying agent (anhydrous magnesium sulfate)
  5. filtrationThe mixture is filtered
  6. concentrationconcentrated
  7. customthe resulting residue is chromatographed (n-hexane/ethyl acetate=12:1) on silica gel column

출처 및 근거

ORD 기록
ord-71602d30b186446786ec942a124881b0
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292911

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