HCID 13904797, compound → HCID 14459369, compound

HRID 1904405Notes

Reaction equation

HRID 1904405 reaction equation
[Br-].[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:9][CH:8]=1)=[O:6])[CH3:3].CC(C)([O-])C.[K+].[N:39]1([CH2:44][C:45](=O)[CH2:46][O:47][CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[CH:43]=[CH:42][N:41]=[CH:40]1>O1CCCC1>[N:39]1([CH2:44]/[C:45](/[CH2:46][O:47][CH2:48][C:49]2[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=2)=[CH:13]\[C:10]2[CH:9]=[CH:8][C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])=[CH:12][CH:11]=2)[CH:43]=[CH:42][N:41]=[CH:40]1

Participants

5

Reactant 3

HCID 13904797HCID 13904797, compoundHCID 16236583{[4-(Ethoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 14459369HCID 14459369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension containing [[4-(ethoxycarbonyl)phenyl]methyl]triphenylphosphonium bromide (11.8 g, 0.0234 mol) in dry tetrahydrofuran (25 ml) at 0° C. under a nitrogen atmosphere was treated with potassium t-butoxide (2.58 g, 0.023 mol). The mixture was allowed to warm up to room temperature and stirred for an additional 90 minutes. The resulting orange mixture was treated with a solution of 1-(1H-imidazol-1-yl)-3-[(4-methoxyphenyl)methoxy]-2-propanone (7.1 g, 0.0273 mol) in dry tetrahydrofuran (25 ml) and stirred for 2 hours. The solvent was evaporated off under reduced pressure and the residue was dissolved in ethyl acetate (300 ml) washed with water (3×150 ml) and extracted into hydrochloric acid (3×200 ml of 5M). The acid solution was basified (K2CO3) and extracted with ethyl acetate (3×250 ml). The extracts were combined, 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 10% hexane in chloroform). The less polar isomer, ethyl 4-[3-(1H-imidazol-1-yl)-2-[[(4-methoxyphenyl)methoxy]methyl]-1E-propenyl]benzoate was obtained as a colourless oil having the following structural characteristics:

Workup

  1. stirringstirred for 2 hours
  2. customThe solvent was evaporated off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (300 ml)
  4. washwashed with water (3×150 ml)
  5. extractionextracted into hydrochloric acid (3×200 ml of 5M)
  6. extractionextracted with ethyl acetate (3×250 ml)
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was evaporated off under reduced pressure
  9. customto yield a crude product
  10. customThe crude product was purified by column chromatography (silica gel 10% hexane in chloroform)

Sources & evidence

ORD record
ord-cafb4c926b9d4ba5949a1838ea65295d
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

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