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

HRID 892638

Reaction equation

HRID 892638 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-41390bbdb22e460ea3992b7be9042a53
Source dataset
uspto-grants-1992_06
Patent number
US05118827

Linked notes

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