Acetyl chloride → HCID 23434070, compound

HRID 1004165Notes

Reaction equation

HRID 1004165 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH3:8])=[CH:5][C:6]=1[CH3:7].[C:9](Cl)(=[O:11])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-]>>[C:9]([C:5]1[C:6]([CH3:7])=[C:2]([Cl:1])[S:3][C:4]=1[CH3:8])(=[O:11])[CH3:10]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12875260HCID 12875260, compound

Product 1

HCID 23434070HCID 23434070, compoundYield 73%

Procedure

To a stirred solution of 2-chloro-3,5-dimethylthiophene (0.9 g, 6.18 mmol) in petroleum ether (5 mL) was added acetyl chloride (0.9 mL, 12.4 mmol) and aluminum chloride (0.99 g, 7.42 mmol) at room temperature under nitrogen, and the mixture stirred for 1 day. The reaction mixture was poured into ice water (50 mL) and the whole was extracted with diethyl ether (70 mL×2). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane-ethyl acetate (20:1) to provide the title product (0.85 g, 73% yield).

Workup

  1. extractionthe whole was extracted with diethyl ether (70 mL×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-dbfe3e5a403443b785cef6df4fa28476
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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