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

HRID 1774595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774595
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178425456HCID 178425456, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%)

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-cdcc1ad6f6da4def8cadc39dc6ab0069
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260395B2

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