Water → HCID 53873716, compound

HRID 1886198Notes

Reaction equation

HRID 1886198 reaction equation
[CH3:1][CH:2]([C:4](=[CH:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[C:5](OCC)=[O:6])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.O>C1(C)C=CC=CC=1>[CH3:3][CH:2]([C:4](=[CH:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:17])[CH3:18])[CH2:5][OH:6])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 21225700DiisobutylaluminumhydrideHCID 54543787HCID 54543787, compound

Product 1

HCID 53873716HCID 53873716, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-72 °C

Procedure

To a solution of ethyl 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienate (280 mg, 1.14 mmol) in toluene (5 ml) chilled at -72° C. under argon atmosphere was dropwise added 0.92M solution of diisobutylaluminum hydride in hexane (3.72 ml, 3.42 mmol). After stirring at -72° C. for 10 minutes, the reaction mixture was mixed with water (1.5 ml) for stopping the reaction. The reaction mixture was vigorously stirred at room temperature for 1 hour, and precipitates were filtered off. The filtrate was concentrated and the residue was chromatographed on a silica gel column to give 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrien-1-ol (214 mg, 84%).

Workup

  1. customthe reaction
  2. stirringThe reaction mixture was vigorously stirred at room temperature for 1 hour
  3. customprecipitates
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated
  6. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-2dccb463792642bb83c8ae7ebcb772b7
Source dataset
uspto-grants-1992_09
Patent number
US05149843

Reaction notes

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