Ethoxalyl chloride → Ethyl 2-oxo-2-(2-phenyl-1-benzothiophen-3-yl)acetate

HRID 590957Notes

Reaction equation

HRID 590957 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:9]1([C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[O:8]=[C:2]([C:19]1[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[S:16][C:15]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 6108862-Phenyl-1-benzothiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 70813788Ethyl 2-oxo-2-(2-phenyl-1-benzothiophen-3-yl)acetateYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chlorooxoacetate (162 μL, 1.45 mmol) was added at 0° C. to a solution of 2-phenyl-1-benzothiophene (2a) (310 mg, 1.46 mmol) and aluminum chloride (III) (389 mg, 2.92 mmol) in dichloromethane (10 mL). After 30 minutes, the reaction mixture was quenched with a saturated aqueous solution of sodium carbonate. The aqueous layer was extracted with ethyl acetate (2×20 mL) and the organic layer was washed with water (20 mL), brine (20 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product (2b) as a pale oil (370 mg, 1.19 mmol, 70%).

Workup

  1. customthe reaction mixture was quenched with a saturated aqueous solution of sodium carbonate
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. washthe organic layer was washed with water (20 mL), brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-229e9d534c014deba828f9e91bde049b
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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