Ethanol → 2-(Benzo[b]thiophen-3-yl)ethanol
Reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][C:7](O)=[O:8])[C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2.[Li].C(O)C>O1CCCC1>[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]1=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of benzo[b]thiophen-3-yl-acetic acid (6.0 g, 31.2 mmol) in 40 ml of tetrahydrofuran was added dropwise at RT to a suspension of lithium alanate (1.54 g, 41 mmol) in 35 ml of tetrahydrofuran. The mixture was stirred for 60 minutes at 60° C., and then excess alanate was hydrolysed with ethanol. The mixture was suction-filtered over Kieselguhr and the solvent was removed in vacuo. The product was obtained in the form of a yellowish oil in a yield of 5.1 g (92%).
Workup
- filtrationThe mixture was suction-filtered over Kieselguhr
- customthe solvent was removed in vacuo
- customThe product was obtained in the form of a yellowish oil in a yield of 5.1 g (92%)
Sources & evidence
- ORD record
- ord-7d496dbea50649b3ba257d028bad7c01
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776848B2
Reaction notes
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