Allyltrimethylsilane → (3RS,4RS)-4-allyl-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792370노트

반응식

HRID 1792370 반응식
O[CH:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[S:5][CH2:4][C:3]1([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:14].[CH2:23]([Si](C)(C)C)[CH:24]=[CH2:25]>ClCCCl.[I-].[Zn+2].[I-]>[CH2:25]([CH:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[S:5][CH2:4][C:3]1([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:14])[CH:24]=[CH2:23]

참가 물질

5

반응물 2

HCID 69808AllyltrimethylsilaneHCID 220333534-Hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

생성물 1

HCID 22033345(3RS,4RS)-4-allyl-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman수율 74.4%

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (11.4 g, 36.3 mmol) in 1,2-dichloroethane (360 ml) was added zinc iodide (13.9 g, 43.5 mmol) and allyltrimethylsilane (11.5 ml, 72.5 mmol) which was stirred for 1 day at room temperature. The reaction solution was added saturated aqueous NHCl solution, extracted with CHCl3, and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica-gel with 1% AcOEt in hexane to give 9.19g (74%) of (3RS,4RS)-4-allyl-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman.

후처리

  1. additionThe reaction solution was added saturated aqueous NHCl solution
  2. extractionextracted with CHCl3
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by chromatography on silica-gel with 1% AcOEt in hexane

출처 및 근거

ORD 기록
ord-6665b512621e40c1aae7183b5bfa7284
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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