Epibromohydrin → HCID 21474728, compound

HRID 1901702Notes

Reaction equation

HRID 1901702 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.[H-].[Na+]>CN(C)C=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH:15]2[CH2:16][O:17]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 615235-Phenyl-1-pentanol

Product 1

HCID 21474728HCID 21474728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 5 g of 5-phenyl-1-pentanol, 4.99 ml of epibromohydrin, 1.31 g of sodium hydride (as a 55% by weight dispersion in mineral oil) and 80 ml of anhydrous dimethylformamide were used. The resulting crude product was purified by silica gel column chromatography, using a 1:6 by volume mixture of ethyl acetate and hexane as the eluent, to give 4.2 g of the title compound as a colorless oil having an Rf value of 0.49 (on silica gel thin layer chromatography, using a 1:4 by volume mixture of ethyl acetate and hexane 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 ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-3907060147ee45039d008c3f7921a4fd
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

Loading…