Water → HCID 14249923, compound

HRID 867751Notes

Reaction equation

HRID 867751 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:12])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[C:13](Cl)(=[O:15])[CH3:14].[Sn](Cl)(Cl)(Cl)Cl.O>C(Cl)Cl>[CH3:1][C:2]1[S:3][C:4]([CH3:12])=[C:5]([C:13](=[O:15])[CH3:14])[C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 14249922HCID 14249922, compound

Product 1

HCID 14249923HCID 14249923, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 2,5-dimethyl-3-thiophene acetate (33.2 g, 0.18 mol) in CH2Cl2 (150 ml) was added to a solution of acetylchloride (15.5 ml, 0.216 mol) and tin (IV) chloride (23.2 ml, 0.198 mol) in CH2Cl2 (200 ml) at 0°-5° C. over a 15 minute period. The solution became a deep red color and was stirred at 0°-5° C. for two hours. H2O (200 ml) was added to the mixture, and the organic layer was separated, washed with saturated aqueous NaHCO3 (1×100 ml), dried over MgSO4, and treated with activated charcoal. The solvent was removed in vacuo to give the product (40.2 g, 97% yield) as an oil with crystallized slowly on standing; mp 68°-71° C.; IR (KBr) 1745 and 1650 cm-1 ; mass spectrum m/z 226 (M+); 1H NMR (CDCl3) δ 2.30 (s, 3H, thiophene-CH3), 2.47 (s, 3H, COCH3), 2.60 (s, 3H, thiophene-CH3), 3.67 (s, 5H, CH2CO2CH3).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous NaHCO3 (1×100 ml)
  3. dry with materialdried over MgSO4
  4. additiontreated with activated charcoal
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e8d09b9cc87b4e288d423958a36b3a14
Source dataset
uspto-grants-1988_10
Patent number
US04775757

Reaction notes

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