Water → HCID 53889773, compound
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](OC)=[O:26].O>ClCCl>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Di-isobutylaluminium hydride (1.0M in dichloromethane, 308 ml, 308 mmol) was injected into a stirred solution of methyl 7-(2,4-dichlorophenyl)-6-heptenoate (40.2 g, 140 mmol) in dichloromethane (200 ml) at -78° C. under argon. After 5 min, the solution was warmed to 0° C., stirred for 0.5 h, then cooled again to -78° C. Water (102 ml) was injected slowly, while allowing the mixture to warm to room temperature. When solid had precipitated, ethyl acetate (400 ml) was added, then excess NaHCO3, and the mixture stirred vigorously for 0.25 h. The solids were filtered off, the solvent removed under vacuum, and the residue purified by chromatography on silica gel (30-70% ether/petroleum ether 40°-60° C.) to give the title compound (31.7 g, 85%) as an oil, comprising a mixture of E and Z isomers.
Workup
- temperaturecooled again to -78° C
- temperatureto warm to room temperature
- customWhen solid had precipitated
- additionethyl acetate (400 ml) was added
- stirringexcess NaHCO3, and the mixture stirred vigorously for 0.25 h
- filtrationThe solids were filtered off
- customthe solvent removed under vacuum
- customthe residue purified by chromatography on silica gel (30-70% ether/petroleum ether 40°-60° C.)
Sources & evidence
- ORD record
- ord-db02716744434c43ae10e11df4aa4720
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05447954
Reaction notes
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