Ethanol → 2-Cyano-3-hydroxymethylthiophene

HRID 1952840Notes

Reaction equation

HRID 1952840 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

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 122800084-Formylthiophene-2-carbonitrile

Product 1

HCID 218664902-Cyano-3-hydroxymethylthiopheneYield 91.5%

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

  1. customslowly formed a clear solution
  2. concentrationThe residue after concentration under reduced pressure
  3. washwashed successively with saturated brine, 5% strength citric acid and saturated brine
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c59f81e6c3b413f916c26efaee5a75f
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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