HCID 14403241, compound → HCID 14154194, compound

HRID 621824Notes

Reaction equation

HRID 621824 reaction equation
[Br:1][C:2]1[C:3]([S:14][CH:15]([CH3:17])[CH3:16])=[C:4]([C:8]([O:10]C(C)C)=[O:9])[S:5][C:6]=1[CH3:7]>CO.[OH-].[Na+]>[Br:1][C:2]1[C:3]([S:14][CH:15]([CH3:17])[CH3:16])=[C:4]([C:8]([OH:10])=[O:9])[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 1

HCID 14403241HCID 14403241, compound

Product 1

HCID 14154194HCID 14154194, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-Methylethyl 4-bromo-5-methyl-3-[(1-methylethyl)thio]-2-thiophenecarboxylate (11.1 g, 33 mmoles) is stirred under argon in a mixture of methanol (10 mL) and 1N sodium hydroxide (70 mL), and heated under reflux. After 4.5 hours the mixture is cooled, stirred into ice water (300 mL) and extracted twice with ether (50 mL). The aqueous layer is acidified with concentrated HCl and the precipitate is filtered off, rinsed with water and dried to afford the product (8.4 g); mp 132°-134° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureAfter 4.5 hours the mixture is cooled
  4. extractionextracted twice with ether (50 mL)
  5. filtrationthe precipitate is filtered off
  6. washrinsed with water
  7. customdried

Sources & evidence

ORD record
ord-97b81b722cc14c06a5372daaed111e8a
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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