Methyl (methylsulfinyl)methyl sulfide → 2-Chloro-1-methoxy-3-[2-(methylsulfanyl)-2-(methylsulfinyl)vinyl]benzene

HRID 28509

반응식

HRID 28509 반응식
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][S:13][CH2:14][S:15]([CH3:17])=[O:16]>C1COCC1>[Cl:1][C:2]1[C:3]([CH:4]=[C:14]([S:13][CH3:12])[S:15]([CH3:17])=[O:16])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

참가 물질

4

반응물 2

HCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 125756952-Chloro-3-methoxybenzaldehyde

생성물 1

HCID 865965082-Chloro-1-methoxy-3-[2-(methylsulfanyl)-2-(methylsulfinyl)vinyl]benzene수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-chloro-3-methoxybenzaldehyde 7a (4.65 g, 27.3 mmol) and methyl (methylthio)methyl sulfoxide (4.3 mL, 43.9 mmol) in THF (25 mL) was added a 40% methanolic solution of Triton B (6.2 mL, 13.6 mmol) and the resulting solution was refluxed for 16 hours. After THF was removed, the residue was taken up in ethyl acetate,washed with 1 N HCl, H2O, and brine, then was dried over Na2SO4, and concentrated. Purification by column chromatography on silica gel with dichloromethane afforded 2-chloro-1-methoxy-3-[2-methylsulfanyl)-2-(methylsulfinyl)vinyl]benzene 7b (3.61 g, 48%) as a yellow oil. GCMS (EI) m/z 225 (M+-Cl16), 210 (M+-Cl-OMe).

후처리

  1. temperaturethe resulting solution was refluxed for 16 hours
  2. customAfter THF was removed
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel with dichloromethane

출처 및 근거

ORD 기록
ord-16169f1d72cb421ba0df70e5d7011029
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419983B2

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