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

HRID 1774595Notes

Reaction equation

HRID 1774595 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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%)

Workup

  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)

Sources & evidence

ORD record
ord-cdcc1ad6f6da4def8cadc39dc6ab0069
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

Loading…