Ethanol → 2-Cyano-3-hydroxymethylthiophene
Reaction equation
[BH4-].[Na+].[C:3]([C:5]1[S:6][CH:7]=[C:8](C=O)C=1)#[N:4].[CH2:12]([OH:14])[CH3:13]>>[C:3]([C:5]1[S:6][CH:7]=[CH:8][C:13]=1[CH2:12][OH:14])#[N:4]Participants
4
Procedure
3.47 g (91.8 mmol) of sodium borohydride were added in portions to a suspension of 12.6 g (91.8 mmol) of 2-cyano-4-formylthiophene in 200 ml of ethanol, and the reaction mixture was stirred at room temperature for 2 h, during which it slowly formed a clear solution. The residue after concentration under reduced pressure was taken up in ethyl acetate and washed successively with saturated brine, 5% strength citric acid and saturated brine, and the organic phase was dried with sodium sulfate and concentrated under reduced pressure to result in 11.7 g of almost pure product (yield 91.5%).
Workup
- customslowly formed a clear solution
- concentrationThe residue after concentration under reduced pressure
- washwashed successively with saturated brine, 5% strength citric acid and saturated brine
- dry with materialthe organic phase was dried with sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0c59f81e6c3b413f916c26efaee5a75f
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114358
Reaction notes
Loading…