Methyl iodide → 2,2-Difluoro-1-benzyloxy-5-methoxypentane

HRID 568978Notes

Reaction equation

HRID 568978 reaction equation
CI.[F:3][C:4]([F:18])([CH2:14][CH2:15][CH2:16][OH:17])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:19]C(C)([O-])C.[K+]>O1CCCC1>[F:3][C:4]([F:18])([CH2:14][CH2:15][CH2:16][O:17][CH3:19])[CH2:5][O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 201494602,2-Difluoro-1-benzyloxy-5-hydroxypentaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 201494942,2-Difluoro-1-benzyloxy-5-methoxypentane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Excess methyl iodide (17 g, 120 mmoles) is added to the alcoholate previously prepared from 2,2-difluoro-1-benzyloxy-5-hydroxypentane (9.8 g, 42.6 mmoles) and potassium t-butoxide (5.6 g, 50 mmoles) in dry tetrahydrofuran (50 ml). The reaction mixture is kept at room temperature overnight, concentrated under vacuum, and the residue is deluted with water and ether. Usual extraction gives the title compound which is purified by chromatography on silica (ethyl acetate/petroleum ether: 20/80, RF: 0.9; 7.4 g, 71%).

Workup

  1. concentrationconcentrated under vacuum
  2. extractionUsual extraction

Sources & evidence

ORD record
ord-65defd26fa3a47abbc268e6a59857cd5
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

Loading…