Triethylamine → 2,2-Difluoro-5-methoxypentan-1-ol

HRID 568979Notes

Reaction equation

HRID 568979 reaction equation
C[Si](I)(C)C.[F:6][C:7]([F:22])([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH2:8][O:9]CC1C=CC=CC=1.C(N(CC)CC)C>ClCCl>[F:6][C:7]([F:22])([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 201494942,2-Difluoro-1-benzyloxy-5-methoxypentane

Product 1

HCID 140975992,2-Difluoro-5-methoxypentan-1-olYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyliodide (5.2 g, 26 mmoles) is added to a solution of 2,2-difluoro-1-benzyloxy-5-methoxypentane (6.3 g, 25.8 mmoles) in dry dichloromethane (30 ml), kept under nitrogen at room temperature. After standing for 1 hour at 25° C., the reaction mixture is treated with triethylamine (5 ml) during 1 hour, diluted with dichloromethane and washed with 1N HCl and twice with diluted brine. Bulb to bulb distillation of the crude oil obtained (4.2 g) (110°-150° C., 15 mm) gives the title compound (2.7 g, contaminated with 10% of 2,2-difluoro-1-benzyloxy-5-hydroxy pentane).

Workup

  1. customkept under nitrogen at room temperature
  2. washwashed with 1N HCl and twice with diluted brine
  3. distillationBulb to bulb distillation of the crude oil
  4. customobtained (4.2 g) (110°-150° C., 15 mm)

Sources & evidence

ORD record
ord-34a24940a15c47168cff0f4638222e1b
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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