Ethyl Acetoacetate → Methyl 3-hydroxy-5-methylthiophene-2-carboxylate

HRID 621783Notes

Reaction equation

HRID 621783 reaction equation
[C:1]([O:7][CH2:8]C)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[C:10](OC)(=O)[CH2:11][SH:12].[Na]>ClCCl>[OH:4][C:3]1[CH:5]=[C:11]([CH3:10])[S:12][C:2]=1[C:1]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 16907Methyl ThioglycolateHCID 5360545Sodium

Product 1

HCID 587860Methyl 3-hydroxy-5-methylthiophene-2-carboxylateYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared by the method described in Example 1 from ethyl acetoacetate (130 g, 1.0 mole), methyl thioglycolate (212 g, 2.0 moles) and sodium (53 g, 2.3 moles). The crude product is shaken with two portions of dichloromethane, filtered, and the filtrate stripped of solvent under reduced pressure to afford the product (90.1 g); mp 50°-53° C.

Workup

  1. customPrepared by the method
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a0d5afd534c549998c46e0ca23cb59e2
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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