HCID 15588103, compound → Methyl 4-chloro-3-hydroxythiophene-2-carboxylate

HRID 1200104Notes

Reaction equation

HRID 1200104 reaction equation
Cl[C:2]1([C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:7])[C:5]([Cl:8])=[CH:4][S:3]1>C(O)(=O)C.[Zn]>[Cl:8][C:5]1[C:6]([OH:7])=[C:2]([C:9]([O:11][CH3:12])=[O:10])[S:3][CH:4]=1

Participants

4

Reactant 1

HCID 15588103HCID 15588103, compound

Product 1

HCID 54706808Methyl 4-chloro-3-hydroxythiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2,4-Dichloro-2-methoxycarbonylthiophene-3(2H)-one (60 mmol) in acetic acid (50 ml) was treated with metallic zinc (60 mmol) at room temperature for 18 hours. The solvent was removed under reduced pressure and the residue partitioned between water and ether. The organic phase was washed with water, dried with sodium sulphate and the solvent removed under reduced pressure to leave a solid which was crystallised from hexane m.p. 76°-77° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between water and ether
  3. washThe organic phase was washed with water
  4. dry with materialdried with sodium sulphate
  5. customthe solvent removed under reduced pressure
  6. customto leave a solid which
  7. customwas crystallised from hexane m.p. 76°-77° C.

Sources & evidence

ORD record
ord-90b2f277360440e4b238740d48925f0d
Source dataset
uspto-grants-1990_02
Patent number
US04904686

Reaction notes

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