Epibromohydrin → HCID 13232001, compound

HRID 2294325Notes

Reaction equation

HRID 2294325 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:14]([CH:16]1[O:18][CH2:17]1)Br>CN(C)C=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:14][CH:16]2[CH2:17][O:18]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 76889Benzenebutanol

Product 1

HCID 13232001HCID 13232001, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 5.00 g of 4-phenyl-1-butanol, 1.58 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 3.9 ml of epibromohydrin and 110 ml of anhydrous dimethylformamide were used. The resulting crude product was purified by silica gel column chromatography, using an 8:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.83 g of the title compound as a colorless oil having an Rf value of 0.77 (on silica gel thin layer chromatography, using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 46
  2. customThe resulting crude product was purified by silica gel column chromatography
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-59b5107c01de475b978172281276d7cd
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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