Ethanol → 4-[2-(8-Phenyl-2-naphthalenyl)-propenyl]benzoic acid, ethyl ester

HRID 259904Notes

Reaction equation

HRID 259904 reaction equation
C(OP([CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)(OCC)=O)C.[C:20]1([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]3[C:35]=2[CH:34]=[C:33]([C:36](=O)[CH3:37])[CH:32]=[CH:31]3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O-][CH2:40]C.[Na+].C(O)C>CS(C)=O.C(=O)(O)[O-].[Na+]>[C:20]1([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]3[C:35]=2[CH:34]=[C:33]([C:36]([CH3:37])=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH2:17][CH3:40])=[O:15])=[CH:18][CH:19]=2)[CH:32]=[CH:31]3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 10946061Methyl 4-(diethoxyphosphorylmethyl)benzoateHCID 224042281-(8-Phenyl-2-naphthyl)ethanone

Product 1

HCID 867495374-[2-(8-Phenyl-2-naphthalenyl)-propenyl]benzoic acid, ethyl esterYield 64%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Methyl p-[(diethoxyphosphoryl)methyl]benzoate (4.00 g, 13.97 mmoles, prepared as in Liebigs Ann. Chem. 1985, 929) was added to a 1M dimsyl anion solution in dimethylsulfoxide (12.71 mL,12.71 mmoles, prepared by warming sodium hydride in dimethylsulfoxide for 1 hour at 65° C.). After 30 minutes, the mixture was added to a solution of 1-(8-phenyl-2-naphthyl)ethanone (XIVa) (0.540 g, 2.19 mmoles) in dimethylsulfoxide (10.0 mL) at room temperature. After 2 hours at room temperature, a 1M solution of sodium ethoxide in ethanol (1.31 mL, 2.63 mmoles) was added. After 2 hours at room temperature, the mixture was diluted with saturated sodium bicarbonate (100 mL) and extracted with diethyl ether (100 mL×3). The solution was evaporated and the residue chromatographed (eluted with 5% ethyl acetate in hexane) over silica to give 0.500 g (yield: 64%) of 4-[2-(8-phenyl-2-naphthalenyl)-propenyl]benzoic acid, ethyl ester as a white solid. NMR indicated the ratio of E to Z isomers as 2:1.

Workup

  1. waitAfter 2 hours at room temperature
  2. waitAfter 2 hours at room temperature
  3. extractionextracted with diethyl ether (100 mL×3)
  4. customThe solution was evaporated
  5. customthe residue chromatographed
  6. wash(eluted with 5% ethyl acetate in hexane) over silica

Sources & evidence

ORD record
ord-dadb997b766e4ef6952210491c8aaca6
Source dataset
uspto-grants-1996_06
Patent number
US05523457

Reaction notes

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