Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 67459847, compound

HRID 554862Notes

Reaction equation

HRID 554862 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]=O)[N:6]=1.[CH3:9][O:10][C:11](=[O:32])[CH:12]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1.O>[CH3:9][O:10][C:11](=[O:32])[CH:12]=[CH:7][C:5]1[N:6]=[C:2]([Br:1])[S:3][CH:4]=1

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 177504332-Bromo-1,3-thiazole-4-carboxaldehyde

Product 1

HCID 67459847HCID 67459847, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-bromothiazole-4-carbaldehyde (3.00 g, 15.62 mmol) in tetrahydrofuran (52 mL) and add methyl(triphenylphosphoranylidene)acetate (5.33 g. 15.62 mmol). Stir the mixture overnight at room temperature. Dilute the mixture with water and extract twice using diethyl ether. Dry the combined organics over sodium sulfate, filter, and concentrate. Purify via silica gel chromatography using a 0-30% gradient of EtOAc/hexanes to give 3.13 g (81%) of the title compound as a white solid.

Workup

  1. extractionextract twice using diethyl ether
  2. dry with materialDry the combined organics over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify via silica gel chromatography

Sources & evidence

ORD record
ord-16f76a513b1c41c283f69bb220b0c352
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

Loading…