(Carbethoxyhexyl)triphenylphosphonium bromide → Ethyl 8-[(1H-imidazol-1-yl)methyl]-11-(4-methoxyphenyl)-7-undecenoate

HRID 1904411Notes

Reaction equation

HRID 1904411 reaction equation
[Br-].[CH2:2]([O:4][C:5](=[O:31])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:3].CC(C)([O-])C.[K+].[N:38]1([CH2:43][C:44](=O)[CH2:45][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)[CH:42]=[CH:41][N:40]=[CH:39]1>O1CCCC1>[N:38]1([CH2:43][C:44]([CH2:45][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:31])[CH:42]=[CH:41][N:40]=[CH:39]1

Participants

5

Reactant 3

HCID 10994694(Carbethoxyhexyl)triphenylphosphonium bromideHCID 14459374HCID 14459374, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 53704658Ethyl 8-[(1H-imidazol-1-yl)methyl]-11-(4-methoxyphenyl)-7-undecenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension containing (7-ethoxy-7-oxoheptyl) triphenylphosphonium bromide (12 g, 0.024 mol) in dry tetrahydrofuran (40 ml) at room temperature under a nitrogen atmosphere was treated with potassium t-butoxide (2.70 g, 0.024 mol). The resulting orange mixture was stirred for 1 hour, treated with a solution of 1-(1H-imidazol-1-yl)-5-(4-methoxyphenyl)-2-pentanone (5.0 g, 0.019 mol) in dry tetrahydrofuran (20 ml) and then stirred for an additional 14 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 (4×150 ml of 5M). The acid extracts were combined, washed with ethyl acetate, basified using sodium carbonate, and extracted with ethyl acetate (4×250 ml). The organic 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, 40% ethyl acetate in hexane to 100% ethyl acetate) to yield an isomeric mixture of E- and Z-ethyl 8-[(1H-imidazol-1-yl)methyl]-11-(4-methoxyphenyl)-7-undecenoate as a pale-yellow oil having the following structural characteristics:

Workup

  1. stirringstirred for an additional 14 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 (4×150 ml of 5M)
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate (4×250 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-a83554ce0488491da43e9a7547d1e949
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

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