Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 69886837, compound

HRID 1635971Notes

Reaction equation

HRID 1635971 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]=O.[C:9]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:11][CH2:12][CH3:13])=[O:10]>C1COCC1>[CH2:12]([O:11][C:9](=[O:10])/[CH:14]=[CH:7]/[C:6]1[CH:5]=[CH:4][S:3][C:2]=1[Br:1])[CH3:13]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 122459212-Bromothiophene-3-carbaldehyde

Product 1

HCID 69886837HCID 69886837, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the aldehyde of Example 23(c) (4.334 g, 22.7 mmol) and (carboethoxymethylene)triphenylphosphorane (8.708 g, 25.0 mmol, Aldrich) in THF (40 mL) was stirred for 17 h. The solution was then evaporated, taken into ether (53 mL) and vacuum filtered. The filtrate was evaporated and the residue purified by flash chromatography on silica gel (20% ethyl acetate/hexanes) to give (E)-3-(2-Bromo-thiophen-3-yl)-acrylic acid ethyl ester 4 (5.559 g, 21.3 mmol, 94%) as a slightly yellow oil.

Workup

  1. customThe solution was then evaporated
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue purified by flash chromatography on silica gel (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b6d27d8a4791463992b2f2e7c92faa95
Source dataset
uspto-grants-2003_01
Patent number
US06511999B2

Reaction notes

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