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

HRID 2084351Notes

Reaction equation

HRID 2084351 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-27d66a16b2c94b1a93cc1413a7ee9cb4
Source dataset
uspto-grants-2004_04
Patent number
US06716864B2

Reaction notes

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