Sodium hydride → 8-(3,4-Difluoro-benzyloxy)-octan-1-ol

HRID 1802955Notes

Reaction equation

HRID 1802955 reaction equation
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[H-].[Na+].[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:17]Br>O1CCCC1.CN(C)C=O.CN(C)C=O>[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:17][O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:10]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 694201,8-OctanediolHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 668746338-(3,4-Difluoro-benzyloxy)-octan-1-olYield 46.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A solution of 1,8-octanediol (300 mg, 2.05 mmol) in tetrahydrofuran/N,N-dimethylformamide 2:1 (3 mL) was added dropwise at 0° C. to a suspension of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.3 mmol) in N,N-dimethylformamide (1.5 mL), then after 2 h 3,4-difluorobenzyl bromide (445 mg, 2.15 mmol) was added. After 4 h the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded 8-(3,4-difluoro-benzyloxy)-octan-1-ol (258 mg, 46%). Colorless oil, m/e=273.3 ([M+H]+).

Workup

  1. customAfter 4 h the reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5b712868cafb468b9e8f634095389f38
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

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