3-Methoxyphenol → HCID 19754897, compound

HRID 1588914Notes

Reaction equation

HRID 1588914 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH:7]([N:10]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:11](=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Br)=[C:14]([O:20][CH3:21])[CH:13]=1)([CH3:9])[CH3:8].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1>CN(C)C=O.O>[CH:23]1([N:10]([CH:7]([CH3:9])[CH3:8])[C:11](=[O:22])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][O:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([O:30][CH3:29])[CH:32]=3)=[C:14]([O:20][CH3:21])[CH:13]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 99990804-Bromomethyl-3-methoxy-N-cyclohexyl-N-isopropylbenzamide

Product 1

HCID 19754897HCID 19754897, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A slurry of K2CO3 (0.75 g, 5.43 mmol) in a solution of 4-bromomethyl-3-methoxybenzoic acid N-isopropyl-N-cyclohexyl amide (1.0 g, 2.7 mmol) and 3-methoxy phenol (0.35 g, 2.74 mmol) in dimethylformamide (DMF) (15 ml) was stirred overnight at room temperature. The reaction mixture was diluted with water (50 ml), extracted twice with ethyl acetate and dried (Na2SO4) The drying agent was filtered and the filtrate concentrated in vacuo to give the crude product as a dark oil. This material was purified by chromatography on silica gel using mixtures of ethyl acetate, CH2Cl2 and hexane as eluents to give the title compound as a glass.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialdried (Na2SO4) The drying agent
  3. filtrationwas filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give the crude product as a dark oil
  6. customThis material was purified by chromatography on silica gel using mixtures of ethyl acetate, CH2Cl2 and hexane as eluents

Sources & evidence

ORD record
ord-5f97a9ce686840dbaab8f93cd438e8bc
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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