Potassium Hydroxide → HCID 20131160, compound

HRID 1380113Notes

Reaction equation

HRID 1380113 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][CH:31]([CH3:33])[CH3:32])=[O:29].[Cl-].[NH4+]>CS(C)=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]([O:30][CH:31]([CH3:32])[CH3:33])=[O:29])[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 549816Isopropyl 6-bromohexanoateHCID 13590265HCID 13590265, compound

Product 1

HCID 20131160HCID 20131160, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-[2-Hydroxy-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (Example 1b; 10 g, 0.038 mol) was added to a stirred suspension of powdered potassium hydroxide (8 g, 0.14 mol) in dimethylsulphoxide (20 ml) at 18° C. and stirred for 0.5 hours. Isopropyl 6-bromohexanoate (10.5 g, 0.044 mol) was then added and the mixture was stirred for 0.5 hours at 18° C. The mixture was poured into saturated aqueous ammonium chloride (1500 ml) and extracted with dichloromethane. The combined extracts were dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crude product which was purified by column chromatography (silica gel, 2% ethanol in chloroform) to give isopropyl 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoate as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred for 0.5 hours at 18° C
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent was evaporated off under reduced pressure
  5. customto give the crude product which
  6. customwas purified by column chromatography (silica gel, 2% ethanol in chloroform)

Sources & evidence

ORD record
ord-b73c89241d3841f9b687a95d2adf7234
Source dataset
uspto-grants-1986_04
Patent number
US04579862

Reaction notes

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