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

HRID 901631

反応式

HRID 901631 の反応式
[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]

参加物

6

反応物 2

HCID 15510CyclopentanethiolHCID 66845200HCID 66845200、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8471Triethylamine溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8676343e98444e898a01cec8a3a9f38
出典データセット
uspto-grants-2008_04
特許番号
US07361787B2

関連ノート

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