Water → HCID 54511971, compound

HRID 1904407Notes

Reaction equation

HRID 1904407 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[N:7]1([CH2:12][C:13](=O)[CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH:11]=[CH:10][N:9]=[CH:8]1.[OH2:26]>O1CCCC1>[N:7]1([CH2:12][C:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:16][CH2:17][CH2:18][CH2:19][CH2:5][C:2]([OH:26])=[O:4])[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 13904797HCID 13904797, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54511971HCID 54511971, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension containing 5-(carboxypentyl) triphenylphosphonium bromide (22 g, 0.048 mol) in dry tetrahydrofuran (100 ml) at 0° C. under a nitrogen atmosphere was treated with potassium t-butoxide (11.2 g, 0.10 mol) and stirred for 2 hours at room temperature. The resulting orange mixture was cooled to 0° C. and treated with a solution of 1-(1H-imidazol-1-yl)-3-[(4-methoxyphenyl)methoxy]-2-propanone (as prepared in Example 1c, 6.4 g, 0.025 mol) in dry tetrahydrofuran (25 ml). The reaction mixture was stirred at room temperature for 4 hours after which time the solvent was evaporated off under reduced pressure to yield a residue which was treated with water (200 ml) and extracted with ethyl acetate (4×150 ml). The aqueous solution was acidified to pH 1 using 12M hydrochloric acid washed with ethyl acetate (3×100 ml), basified to pH 5.5 using sodium bicarbonate and extracted with ethyl acetate (4×150 ml). The extracts were combined, washed with water then brine, dried over sodium sulfate and the solvent was evaporated off under reduced pressure to yield a crude product. The crude product was purified by column chromatography (silica gel, 5% ethanol in chloroform) to yield an isomeric mixture of E- and Z-8-(1-H-imidazol-1-yl)-7-[[(4-methoxyphenyl)methoxy]methyl]-6-octenoic acid as a pale yellow oil having the following structural characteristics:

Workup

  1. temperatureThe resulting orange mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours after which time the solvent
  3. customwas evaporated off under reduced pressure
  4. customto yield a residue which
  5. extractionextracted with ethyl acetate (4×150 ml)
  6. washwashed with ethyl acetate (3×100 ml)
  7. extractionextracted with ethyl acetate (4×150 ml)
  8. washwashed with water
  9. dry with materialbrine, dried over sodium sulfate
  10. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-2cf581d49f7146bbaec27664ebc9ec8a
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

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