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Potassium Hydroxide → 6-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid

HRID 845466
Notes
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Reaction equation

HRID 845466 reaction equation
[OH:1][CH:2]([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[OH-].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]CC)=[O:29]>CS(C)=O.O>[N:4]1([CH2:3][CH:2]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[O:1][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:8]=[CH:7][N:6]=[CH:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 117544Ethyl 6-bromohexanoateHCID 13590265HCID 13590265, compound

Product 1

HCID 135902686-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 962
Water
Solvent

Procedure

1-[2-Hydroxy-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (20 g, 0.076 mol) was added to a stirred suspension of powdered potassium hydroxide (17 g, 0.30 mol) in dimethylsulphoxide (50 ml) at 18° C. and stirred for 0.5 hours. Ethyl 6-bromohexanoate (33.45 g, 0.15 mol) was then added and the resulting mixture was stirred at 18° C. for 12 hours. The reaction mixture was diluted with water (21) and washed with dichloromethane (2×100 ml), neutralised to pH 6-7 with sulphuric acid (2M) and extracted with dichloromethane (4×150 ml). The combined extracts were dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crude product which by column chromatography (silica gel, 20% methanol in ethyl acetate) gave pure 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoic acid as a colourless oil.

Workup

  1. stirringthe resulting mixture was stirred at 18° C. for 12 hours
  2. washwashed with dichloromethane (2×100 ml)
  3. extractionextracted with dichloromethane (4×150 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customthe solvent was evaporated off under reduced pressure
  6. customto give the crude product which by column chromatography (silica gel, 20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-633cea4b5e4843198255f33ec479e1ac
Source dataset
uspto-grants-1988_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04758573

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes