Dimethylformamide → 3-(5-Cyano-2-thiophenyl)-2-propenol

HRID 477172Notes

Reaction equation

HRID 477172 reaction equation
CN(C)C=O.[C:6]([C:8]1[S:12][C:11]([CH:13]=[CH:14][C:15](O)=[O:16])=[CH:10][CH:9]=1)#[N:7].C(Cl)(=O)C(Cl)=O.[BH4-].[Na+]>CCOCC.O1CCCC1>[C:6]([C:8]1[S:12][C:11]([CH:13]=[CH:14][CH2:15][OH:16])=[CH:10][CH:9]=1)#[N:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 4311764Sodium borohydrideHCID 679354333-(5-Cyano-2-thiophenyl)-propenoic acid

Product 1

HCID 571289623-(5-Cyano-2-thiophenyl)-2-propenol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×

Procedure

Dimethylformamide (0.1 ml) was added to a stirred suspension of 3-(5-cyano-2-thiphenyl)-propenoic acid (3.7 g) in dry ether (100 ml) and dry tetrahydrofuran (100 ml) containing oxalyl chloride (2.2 ml). The mixture was stirred for 2 hours then the clear solution was decanted from a little dark tar and evaporated to give the crude acid chloride as a pale solid. A solution of this acid chloride in ether (50 ml) and tetrahydrofuran (50 ml) was added rapidly to a stirred suspension of sodium borohydride doped alumina (3.5 g sodium borohydride on 35 g alumina) in ether (100 ml) with cooling to keep at 15°-20° C. The mixture was stirred for 1 hour and then filtered. The filtrate was evaporated and the residue was chromatographed on silica-gel eluting with ether to give the product as a pale solid.

Workup

  1. customthe clear solution was decanted from a little dark tar
  2. customevaporated
  3. customto give the crude acid chloride as a pale solid
  4. temperaturewith cooling
  5. customto keep at 15°-20° C
  6. stirringThe mixture was stirred for 1 hour
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customthe residue was chromatographed on silica-gel
  10. washeluting with ether

Sources & evidence

ORD record
ord-6ddc92106e9c49908d4fc509e1128862
Source dataset
uspto-grants-1989_12
Patent number
US04886885

Reaction notes

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