Dimethylformamide → 3-Cyanocinnamyl alcohol

HRID 231094Notes

Reaction equation

HRID 231094 reaction equation
CN(C)C=O.[C:6]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[CH:11]=[CH:12][C:13](O)=[O:14])#[N:7].C(Cl)(=O)C(Cl)=O.[BH4-].[Na+]>CCOCC.O1CCCC1>[C:6]([C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[CH:11]=[CH:12][CH2:13][OH:14])#[N:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 4311764Sodium borohydrideHCID 447258693-(3-Cyanophenyl)-2-propenoic acid

Product 1

HCID 537352473-Cyanocinnamyl alcohol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylformamide (0.1 ml) was added to a stirred suspension of 3-cyano-cinnamic acid (30 g) in dry ether (500 ml) containing oxalyl chloride (15 ml). The mixture was stirred for 6 hours, filtered and evaporated to give the crude acid chloride as a pale solid. A solution of this acid chloride in ether (100 ml) and tetrahydrofuran (100 ml) was added to a stirred suspension of sodium borohydride-doped alumina (20 g sodium borohydride on 200 g alumina) in ether (200 ml). The mixture was stirred for 1 hour and then filtered. The filtrate was evaporated and the residue was chromatographed on silica-gel eluting with 2:1 ether:hexane to give the product as a pale oil.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customto give the crude acid chloride as a pale solid
  4. stirringThe mixture was stirred for 1 hour
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customthe residue was chromatographed on silica-gel
  8. washeluting with 2:1 ether

Sources & evidence

ORD record
ord-2f2b9cef091246b99e62be1ab63520bd
Source dataset
uspto-grants-1989_07
Patent number
US04845110

Reaction notes

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