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

HRID 590957ノート

反応式

HRID 590957 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-229e9d534c014deba828f9e91bde049b
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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