Methylcyclopentane → 2-(Cyclopentylidenemethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1774595ノート

反応式

HRID 1774595 の反応式
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.C(/[B:10]1[O:18][C:15]([CH3:17])([CH3:16])[C:12]([CH3:14])([CH3:13])[O:11]1)=C\C>ClCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:2]1(=[CH:1][B:10]2[O:18][C:15]([CH3:17])([CH3:16])[C:12]([CH3:14])([CH3:13])[O:11]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

5

反応物 2

HCID 7296MethylcyclopentaneHCID 113442144,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane

生成物 1

HCID 152600112-(Cyclopentylidenemethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 35%

試薬・触媒・溶媒 2

HCID 178425456HCID 178425456、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of methylcyclopentane (100 mg, 1.22 mmol), and trans-1-propenylboronic acid pinacol ester (204 mg, 1.22 mmol) in dry dichloromethane (6 mL) was bubbled with nitrogen for 5 minutes. Grubbs Catalyst, 2nd generation (52 mg, 0.06 mmol) was added and the reaction mixture was refluxed overnight. The solution was concentrated in vacuo and the residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10) to provide 2-(cyclopentylidenemethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (21a) (88 mg, 0.42 mmol, 35%)

後処理

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10)

出典と根拠

ORDレコード
ord-cdcc1ad6f6da4def8cadc39dc6ab0069
出典データセット
uspto-grants-2016_02
特許番号
US09260395B2

反応ノート

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