Dimethylformamide → HCID 88376545, compound

HRID 1901729Notes

Reaction equation

HRID 1901729 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-57e6a2232d974e0aab6091e8ac2336b2
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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