Tetrahydrofuran → (3-Chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester

HRID 1355013노트

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HRID 1355013 반응식
[CH2:1]([O:3][C:4](=[O:19])[CH:5](OC(=O)C)[C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[C:8]([Cl:14])[CH:7]=1)[CH3:2].[I-].[Sm+3].[I-].[I-].O1CCCC1>CN(C)P(N(C)C)(N(C)C)=O.CO.O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[C:8]([Cl:14])[CH:7]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 8028TetrahydrofuranHCID 10230237Samarium(III) iodideHCID 54200805Acetoxy-(3-chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester

생성물 1

HCID 54095555(3-Chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester수율 60%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 12679Hexamethylphosphoramide용매

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온도
25 °C

실험 절차

A solution of acetoxy-(3-chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester (1.47 g, 4.87 mmol) in hexamethylphosphoramide (7.2 mL) and methanol (20 μL) was treated with a 0.1M solution of samarium iodide in tetrahydrofuran (146 mL, 14.6 mmol). The reaction mixture was stirred at 25° C. under nitrogen for 6 min. During this time period, the reaction mixture changed from purple to white. The reaction mixture was diluted with water (150 mL) and then extracted with methylene chloride (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 4/1 hexanes/ethyl acetate) afforded (3-chloro-4-methylsulfanyl-phenyl)-acetic acid ethyl ester (0.71 g, 60%) as a light yellow oil: EI-HRMS m/e calcd for C11H13ClO2S (M+) 244.0324, found 244.0332.

후처리

  1. extractionextracted with methylene chloride (3×100 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-12844526e928404cb7b23bc1979f5ab9
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223868B2

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