Ethanol → 2-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid
Reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[S:15][C:14](CC#N)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[OH-:19].[K+].[CH2:21]([OH:23])[CH3:22]>O>[OH:23][CH2:21][CH2:22][C:14]1[S:15][C:11]([CH2:10][C:9]([OH:8])=[O:19])=[CH:12][CH:13]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of 2-(5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetonitrile (example 4, step d) (3 g) in ethanol (30 mL) was added to a stirred solution of potassium hydroxide (1.20 g) in water (30 mL). The resulting mixture was stirred at 100° C. for 4 hours. The reaction was concentrated in vacuo and the resulting mixture was partitioned between brine and ethyl acetate. The aqueous layer was cooled with ice, acidified by dropwise addition of concentrated hydrochloric acid and extracted with ethyl acetate three times. The combined organic solutions were washed with brine, dried over sodium sulphate, filtered and the solvent evaporated in vacuo to give the subtitled compound as a yellow solid.
Workup
- concentrationThe reaction was concentrated in vacuo
- customthe resulting mixture was partitioned between brine and ethyl acetate
- temperatureThe aqueous layer was cooled with ice
- additionacidified by dropwise addition of concentrated hydrochloric acid
- extractionextracted with ethyl acetate three times
- washThe combined organic solutions were washed with brine
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-46be980dcec04ed4b319d755fe3704f0
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148373B2
Reaction notes
Loading…