Water → 2-(trans-Styryl)-4-vinyloxazole

HRID 459451Notes

Reaction equation

HRID 459451 reaction equation
[CH2:1]([Li])CCC.[CH:6]([C:8]1[N:9]=[C:10](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:11][CH:12]=1)=O.O.C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH:13](/[C:10]1[O:11][CH:12]=[C:8]([CH:6]=[CH2:1])[N:9]=1)=[CH:14]\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 117357772-Styryloxazole-4-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 227101032-(trans-Styryl)-4-vinyloxazole

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.54N hexane solution, 14.2 ml) was added dropwise to a solution of methyl-triphenylphosphonium bromide (8.16 g) in tetrahydrofuran (80 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled again to 0° C., a solution of 4-formyl-2-(trans-styryl)oxazole (3.64 g) in tetrahydrofuran (20 ml) was added, and the mixture was warmed to room temperature. After stirring for 2 hours, water (200 ml) and ethyl acetate (100 ml) were added and an organic layer was separated. The water layer was extracted with ethyl acetate (50 ml). After the organic layers were combined, washed with saturated saline (100 ml) and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1→3:1) to obtain the title compound (2.84 g) as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled again to 0° C.
  2. temperaturethe mixture was warmed to room temperature
  3. stirringAfter stirring for 2 hours
  4. customan organic layer was separated
  5. extractionThe water layer was extracted with ethyl acetate (50 ml)
  6. washwashed with saturated saline (100 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1→3:1)

Sources & evidence

ORD record
ord-2dbe78f51167471f959910b8e8d23b04
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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