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

HRID 840736Notes

Reaction equation

HRID 840736 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-3e01076d163c4f5db41df64d578e4286
Source dataset
uspto-grants-2002_04
Patent number
US06369089B1

Reaction notes

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