2-(Carboxymethyl)thiophene-3-carboxylic acid → 2-(3-Hydroxymethylthiophen-2-yl)ethanol
Reaction equation
[C:1]([CH2:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10](O)=[O:11])(O)=[O:2]>O1CCCC1>[OH:11][CH2:10][C:9]1[CH:8]=[CH:7][S:6][C:5]=1[CH2:4][CH2:1][OH:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
0.50 g of the compound obtained in Example 4 was dissolved in 10 mL of anhydrous tetrahydrofuran, and the resulting solution was cooled to −20° C. 4 mL of 1.5M solution of borane-tetrahydrofuran complex in tetrahydrofuran was slowly added thereto, and the resulting mixture was allowed to react for at least 1 hour at −10° C. The reaction solution was warmed to room temperature and 4.5 mL of 1.5M solution of borane-tetrahydrofuran complex in tetrahydrofuran was further added thereto. The resulting mixture was kept at room temperature for 1 hour. Thereafter, the procedure of Example 5 was repeated to obtain 0.37 g (yield of 87%) of the title compound as an oil.
Workup
- customto react for at least 1 hour at −10° C
- temperatureThe reaction solution was warmed to room temperature
Sources & evidence
- ORD record
- ord-2cd1b6ec6e274258bffb9d6ab1ce7716
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449580B2
Reaction notes
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