反应 #1692

ord-a1b67cc5004d4967b21c8097f4c0e66d

反应方程式

N#Cc1ccc(C=O)s1
2-cyano-5-formyl-thiophene
[BH4-].[Na+]
sodium borohydride
N#Cc1ccc(CO)s1
2-cyano-5-(hydroxymethyl)thiophene
收率 88.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他the solvent was removed in vacuo
  2. 2
    其他the residue was partitioned between ethyl acetate and brine
  3. 3
    其他The layers were separated
  4. 4
    洗涤the organic phase was washed once with 1M citric acid and once with brine
  5. 5
    干燥dried (MgSO4)
  6. 6
    过滤filtered
  7. 7
    浓缩concentrated in vacuo

实验过程

To a solution of 2-cyano-5-formyl-thiophene (6.9 g, 50 mmol) in EtOH (100 mL) was added sodium borohydride (1.9 g, 50 mmol) in portions. After 5 min of stirring, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and brine. The layers were separated and the organic phase was washed once with 1M citric acid and once with brine, then dried (MgSO4), filtered and concentrated in vacuo to give 6.1 g (88%) of 2-cyano-5-(hydroxymethyl)thiophene.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US05726159uspto-grants-1998_03