Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8](O)=[O:9].O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(2-thienyl)propionic acid (5.0 g, 32.0 mmol) in tetrahydrofuran (20 ml) at 0° C. was added 1 M borane tetrahydrofuran complex (33.5 ml, 33.5 mmol) dropwise over 30 minutes. The reaction mixture was then stirred for 18 h whilst warming to room temperature. The temperature was then reduced to 0° C. and water (20 ml) was added to quench the reaction. The solution was then basified with potassium carbonate, the layers separated and the aqueous layer washed with diethyl ether. The combined organic layers were washed with brine, dried and concentrated to yield the title compound (4.71 g) as an oil. DCI MS m/z 142 [M+H]+.
Workup
- customwas then reduced to 0° C.
- customto quench
- customthe reaction
- customthe layers separated
- washthe aqueous layer washed with diethyl ether
- washThe combined organic layers were washed with brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-829ab7ee72574acab0ebff41a2be95ff
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218538B1
Linked notes
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