(R)-2-Benzhydryloxirane → (2S)-1,1-diphenyl-pent-4-ene-2-ol

HRID 78918Notes

Reaction equation

HRID 78918 reaction equation
[CH:1]([C@@H:14]1[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([Mg]Br)=[CH2:18]>C1COCC1.[Cu]I>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:14]([OH:15])[CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11789056(R)-2-Benzhydryloxirane2×HCID 178418507HCID 178418507, compound

Product 1

HCID 11390776(2S)-1,1-diphenyl-pent-4-ene-2-olYield 70.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

(2R)-2-benzhydryl-oxirane (0.5 g, 2.38 mmol) 23a was dissolved in dry THF (5 ml) and was added into a dry THF solution at −78° C. containing CuI (0.045 g, 0.24 mmol) and vinylmagnesium bromide (5.95 ml of 1.0M solution in THF, 5.95 mmol). The reaction mixture was stirred and allowed to reach room temperature over a period of 2 h, and then quenched with saturated NH4Cl solution. The aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1) to give 0.4 g (2S)-1,1-diphenyl-pent-4-ene-2-ol (70%, [α]D=(−)25, c=1, MeOH).

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×30 ml)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1)

Sources & evidence

ORD record
ord-dbe55d24509644e7b0f7b0f1ae8f8c6f
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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