Cyclopentanethiol → Tert-butyl([3-(cyclopentylthio)benzyl]oxy}dimethylsilane

HRID 503094

반응식

HRID 503094 반응식
[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](I)[CH:11]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([SH:22])[CH2:21][CH2:20][CH2:19][CH2:18]1>CN1CCCC1=O.C(N(CC)CC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:22][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:11]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 15510CyclopentanethiolHCID 66845200Tert-butyl[(3-iodobenzyl)oxy]dimethylsilane

생성물 1

HCID 66845801Tert-butyl([3-(cyclopentylthio)benzyl]oxy}dimethylsilane수율 82.2%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8471Triethylamine용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Tert-butyl[(3-iodobenzyl)oxy]dimethylsilane (WO9513095) (1.44 g) in dry 1-methyl-2-pyrrolidone (15 ml) and triethylamine (4 ml) was stirred at room temperature under nitrogen. 1-1′Bis(diphenylphosphino)ferrocene (110 mg) and tris(dibenzylideneacetone)dipalladium(0) (258 mg) were added and the mixture was stirred for 15 min. Cyclopentyl mercaptan (0.42 g) was then added, and the reaction mixture stirred at 60° C. for 2 h. The reaction mixture was cooled to room temperature, poured onto water and extracted with diethyl ether. The combined organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. The residue was purified on a 50 g SPE, eluting with a stepped gradient of 10 to 100% dichloromethane-cyclohexane to give the title compound (1.09 g) LCMS RT=4.67 min

후처리

  1. stirringthe reaction mixture stirred at 60° C. for 2 h
  2. additionpoured onto water
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified on a 50 g SPE
  7. washeluting with a stepped gradient of 10 to 100% dichloromethane-cyclohexane

출처 및 근거

ORD 기록
ord-3c1d0c72c83c4f92ade1122c2fd59647
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776895B2

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