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

HRID 851102Notes

Reaction equation

HRID 851102 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-ac479e2a1b8947fa9bd57c3a6ad62234
Source dataset
uspto-grants-1983_05
Patent number
US04382929

Reaction notes

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