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

HRID 1774595노트

반응식

HRID 1774595 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178425456HCID 178425456, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-cdcc1ad6f6da4def8cadc39dc6ab0069
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260395B2

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