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

HRID 590957노트

반응식

HRID 590957 반응식
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]

참가 물질

5

반응물 3

HCID 20884Ethoxalyl chlorideHCID 6108862-Phenylbenzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-229e9d534c014deba828f9e91bde049b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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