Acetyl chloride → Methyl 3-thienylacetate

HRID 2199568Notes

Reaction equation

HRID 2199568 reaction equation
[C:1](Cl)(=O)C.[S:5]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6]1>CO>[S:5]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:1])=[O:12])=[CH:6]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 234043-Thiophenacetic acid

Product 1

HCID 94041Methyl 3-thienylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acteyl chloride (7.50 ml, 106 mmol) was added dropwise to a solution of 3-thiopheneacetic acid (5.00 g, 35.3 mmol) in dry MeOH (150 ml) at 0° C. The mixture was left to slowly reach room temperature and stirred overnight. Solvents were evaporated and residue filtered through a short plug of silica gel (DCM) to give a quantitative yield of the title compound as an oil. 1H NMR (400 MHz, CDCl3): □ 3.64 (s, 2H), 3.70 (s, 3H), 7.03-7.05 (m, 1H), 7.14-7.15 (m, 1H), 7.27-7.29 (m, 1H).

Workup

  1. waitThe mixture was left to slowly reach room temperature
  2. customSolvents were evaporated
  3. filtrationresidue filtered through a short plug of silica gel (DCM)

Sources & evidence

ORD record
ord-86e5ab233536434391b1908e724c4ba2
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

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