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

HRID 1609348

Reaction equation

HRID 1609348 reaction equation
[Cl:1][CH2:2][C:3]([CH3:25])=[CH:4][CH2:5][CH2:6][C:7]([CH3:24])=[CH:8][CH2:9][CH2:10][C:11]([CH3:23])=[CH:12][CH:13]=[C:14]([CH:20]([CH3:22])[CH3:21])[C:15](OCC)=[O:16].[H-].C([Al+]C(C)C)(C)C.O.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([CH3:25])=[CH:4][CH2:5][CH2:6][C:7]([CH3:24])=[CH:8][CH2:9][CH2:10][C:11]([CH3:23])=[CH:12][CH:13]=[C:14]([CH:20]([CH3:21])[CH3:22])[CH2:15][OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 21226206Ethyl acetate hexaneHCID 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

Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate (670 mg, 1.81 mmol) was dissolved in dry toluene (20 ml) under argon atmosphere. To the solution cooled on an ethanol-dry ice bath was added with stirring 1M diisopropyl aluminium hydride in toluene (4 ml). After 30 minutes, disappearance of the starting material was confirmed. Water (1.5 ml) was added to the reaction mixture, the cooling bath was removed, and the stirring was continued. After further stirring with addition of MgSO4 as a drying agent, the mixture was filtered and condensed. The resulting residue was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate (12:1)), and relevant fractions gave 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol (492 mg, 79%).

Workup

  1. temperatureTo the solution cooled on an ethanol-dry ice bath
  2. additionwas added
  3. customthe cooling bath was removed
  4. filtrationthe mixture was filtered
  5. customcondensed

Sources & evidence

ORD record
ord-39df3b7b91044b489a030a471579f1a6
Source dataset
uspto-grants-1995_03
Patent number
US05399724

Linked notes

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