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(2S)-2-(4,5-diphenyloxazol-2-yl)oxirane → (4S)-4-(4,5-diphenyloxazol-2-yl)-4-hydroxy-1-butene

HRID 380123
Notes
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Reaction equation

HRID 380123 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@@H:18]3[CH2:20][O:19]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([Mg]Cl)=[CH2:22]>C1COCC1.[Cu]I>[C:1]1([C:7]2[N:8]=[C:9]([C@@H:18]([OH:19])[CH2:20][CH:21]=[CH2:22])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 57131304(2S)-2-(4,5-diphenyloxazol-2-yl)oxiraneHCID 178461836HCID 178461836, compound

Product 1

HCID 56991674(4S)-4-(4,5-diphenyloxazol-2-yl)-4-hydroxy-1-butene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent
2×

Procedure

To a solution of (2S)-2-(4,5-diphenyloxazol-2-yl)oxirane (12 g) and CuI (0.19 g) in THF (240 ml) was dropwise added a solution of vinylmagnesium chloride in THF (1.0M solution, 101 ml) at −78° C. under N2. The mixture was stirred for 1 hour at room temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (4S)-4-(4,5-diphenyloxazol-2-yl)-4-hydroxy-1-butene (9.2 g).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-525d6f3f68c34670aa445f84667745bc
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06300344B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes