2-(5-Chloro-1,3-dihydro-2-benzofuran-1-yl)acetic acid → 2-(5-Chloro-1,3-dihydro-2-benzofuran-1-yl)ethanol
Reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]([CH2:9][C:10](O)=[O:11])[O:7][CH2:8][C:4]=2[CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]([CH2:9][CH2:10][OH:11])[O:7][CH2:8][C:4]=2[CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(5-Chloro-1,3-dihydro-2-benzofuran-1-yl)acetic acid (1.91 g, 9.0 mmol) was dissolved in dry THF (8 mL) under nitrogen and cooled to 0° C. Borane-dimethylsulfide complex (0.155 mL, 1.64 mmol) was added by syringe. After 1 h the cooling bath was removed and the solution was stirred at room temperature for 2 h. The solution was partitioned between saturated aqueous sodium hydrogen carbonate and diethyl ether. The aqueous layer was further extracted with ether, and the combined organic layers washed with brine, dried (MgSO4), filtered and concentrated in vacuo. This yielded the title compound as a white solid (>98% ee by chiral HPLC).
Workup
- additionBorane-dimethylsulfide complex (0.155 mL, 1.64 mmol) was added by syringe
- customAfter 1 h the cooling bath was removed
- customThe solution was partitioned between saturated aqueous sodium hydrogen carbonate and diethyl ether
- extractionThe aqueous layer was further extracted with ether
- washthe combined organic layers washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-979dfce3043c4d37a2d9a222ef4b9e10
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335660B2
Reaction notes
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