Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 66852034, compound

HRID 1668511Notes

Reaction equation

HRID 1668511 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:18]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH:16]=[CH:23][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 58967062HCID 58967062, compound

Product 1

HCID 66852034HCID 66852034, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(t-Butyldimethylsilanyloxymethyl)pyridine-2-carboxaldehyde (4.29 g) was dissolved in 50 mL of DMF, and 7.14 g of (carbethoxymethylene)triphenylphosphorane was added to the solution, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure. To the residue, 100 mL of a mixture of hexane-ethyl acetate (5:1) was added, the insoluble material was filtrated off, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (hexane-ethyl acetate=10:1) to give 5.45 g of ethyl 3-[6-(t-butyldimethylsilanyloxymethyl)pyridin-2-yl]acrylate as a light yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. additionTo the residue, 100 mL of a mixture of hexane-ethyl acetate (5:1) was added
  6. filtrationthe insoluble material was filtrated off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (hexane-ethyl acetate=10:1)

Sources & evidence

ORD record
ord-900c51a3481042b98a53d893bb67e050
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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