Acetone → Methyl 5-(hydroxymethyl)thiophene-3-carboxylate

HRID 867918Notes

Reaction equation

HRID 867918 reaction equation
Cl[CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1.CC(C)=[O:14]>[N+]([O-])([O-])=O.[Ag+]>[OH:14][CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 12926494Methyl 5-(chloromethyl)thiophene-3-carboxylate

Product 1

HCID 12926498Methyl 5-(hydroxymethyl)thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

A solution of methyl 5-(chloromethyl)-3-thiophenecarboxylate (1.7 g) in 50% aqueous acetone (60 ml) was treated with silver nitrate (1.52 g). After 2 h the resulting precipitate was filtered and the filtrate was evaporated. The residue was extracted with diethyl ether, and the ethereal extract was washed with water. Evaporation of the solvent gave an oily residue, which was chromatographed on silica with ethyl acetate-light petroleum 60°-80°; (1:1) to give the title compound as an oil (0.3 g) b.p. 110/0.1 mm m.p. 38°-40°.

Workup

  1. filtrationAfter 2 h the resulting precipitate was filtered
  2. customthe filtrate was evaporated
  3. extractionThe residue was extracted with diethyl ether
  4. extractionthe ethereal extract
  5. washwas washed with water
  6. customEvaporation of the solvent
  7. customgave an oily residue, which
  8. customwas chromatographed on silica with ethyl acetate-light petroleum 60°-80°

Sources & evidence

ORD record
ord-dfd604c7ae6f4e01b5216d315288d5ec
Source dataset
uspto-grants-1988_10
Patent number
US04777179

Reaction notes

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