Dimethylformamide → HCID 88376545, compound

HRID 2294343Notes

Reaction equation

HRID 2294343 reaction equation
CN(C)[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Br.[H-].[Na+].[CH3:18][N:19](C)[CH:20]=O>>[CH3:18][N:19]([CH3:20])[CH:14]1[O:15][CH:13]1[CH2:11][O:9][C:5]1[CH:4]=[CH:3][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 74213-(Dimethylamino)phenolHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 88376545HCID 88376545, compound

Procedure

A procedure similar to that described in Preparation 46 was repeated, except that 4.00 g of 3-dimethylaminophenol, 4.5 ml of epibromohydrin, 1.53 g of sodium hydride (as a 55% by weight dispersion in mineral oil) and 50 ml of dimethylformamide were used. The resulting crude product was purified by silica gel column chromatography, using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent, to give 4.18 g of the title compound having an Rf value of 0.36 (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-5a8061dec7d34c02a491b6254439d7bd
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

Loading…