Diisobutylaluminum hydride → 5-Bromo-2-(2-thienylmethoxy)benzenemethanol
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C[AlH]CC(C)C)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH:11]=1)[CH2:7][OH:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
A solution of methyl 5-bromo-2-(2-thienylmethoxy)benzoate (1.6 g, 4.9 mmol) in dichloromethane (20 ml) was cooled to -85° C. A solution of DIBAL (5.8 ml, 1N in CH2Cl2) was added dropwise. The temperature was maintained below -75° C. for 30 minutes and then warmed to -50° C. over 21/2% hours. The reaction mixture was quenched with 1N HCl, washed with aqueous sodium hydrogen carbonate solution, dried (MgSO4) and evaporated. The product was purified by chromatography (eluant: diethyl ether/hexane) to give 5-bromo-2-(2-thienylmethoxy)benzyl alcohol a colourless gum (0.53 g, 36.4%).
Workup
- temperatureThe temperature was maintained below -75° C. for 30 minutes
- customThe reaction mixture was quenched with 1N HCl
- washwashed with aqueous sodium hydrogen carbonate solution
- dry with materialdried (MgSO4)
- customevaporated
- customThe product was purified by chromatography (eluant: diethyl ether/hexane)
Sources & evidence
- ORD record
- ord-e53d125e41db434381ce0c3b6a668494
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05843942
Reaction notes
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