Sodium ethoxide → HCID 54042628, compound

HRID 2254464Notes

Reaction equation

HRID 2254464 reaction equation
[Cl-].[S:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:30]=[CH:31][CH:32]=2)[CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:3]1.[CH:33]([C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38]O)=[O:34].[O-]CC.[Na+]>C(O)C>[S:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:10]=[CH:38][C:37]3[CH:36]=[C:35]([CH:42]=[CH:41][CH:40]=3)[CH2:33][OH:34])[CH:30]=[CH:31][CH:32]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 131314553-(Hydroxymethyl)benzaldehydeHCID 19744721HCID 19744721, compound

Product 1

HCID 54042628HCID 54042628, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.21 g of the resulting phosphonium salt was dissolved in 45 ml of ethanol, and 0.35 g of 3-formylbenzyl alcohol and 0.27 g of sodium ethoxide were added. The mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure. The residue was distributed between ethyl acetate and water, worked up in a customary manner, and purified by silica gel column chromatography [Wakogel C-300, 100 g; eluting solvent: hexane/ethyl acetate=10/1→5/1] to give 0.34 g (yield 46%) of an E-form of 3-[2-[3-(3-thienyl)-phenyl]ethenyl]benzyl alcohol and 0.34 g of its Z-form.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. custompurified by silica gel column chromatography [Wakogel C-300, 100 g; eluting solvent: hexane/ethyl acetate=10/1→5/1]

Sources & evidence

ORD record
ord-678763fec49142998e2621cb55cac8a5
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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