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

HRID 2369715

반응식

HRID 2369715 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-d75dd3502e0e460c9fe2eefae1782a8c
출처 데이터셋
uspto-grants-2014_04
특허 번호
USRE044874E1

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