Triphenylphosphine → (2S)-2-(Diphenylmethyl)oxirane

HRID 1897901Notes

Reaction equation

HRID 1897901 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:8]([OH:11])[CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1C=CC=CC=1>[CH:7]([C@H:8]1[CH2:9][O:11]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 54762284(2S)-3,3-diphenyl-propane-1,2-diol

Product 1

HCID 11816639(2S)-2-(Diphenylmethyl)oxiraneYield 77.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (2S)-3,3-diphenyl-propane-1,2-diol (3.5 g, 15.35 mmol), Ph3P (8.05 g, 30.7 mmol), and DEAD (5.4 g, 30.7 mmol) in benzene (50 ml) was refluxed for 24 h. Solvent was removed and the residue was diluted with ethyl ether (200 ml) to precipitate Ph2PO. The filtrate was concentrated and the residue was chromatographed on silica gel (hexane/ether=9:1) to give (2S)-2-benzhydryl-oxirane 23b 2.5 g (78%, ([α]D=(−)9.6, c=1, MeOH). The 1HNMR and 13CNMR were identical with (R)-isomer.

Workup

  1. customSolvent was removed
  2. additionthe residue was diluted with ethyl ether (200 ml)
  3. customto precipitate Ph2PO
  4. concentrationThe filtrate was concentrated
  5. customthe residue was chromatographed on silica gel (hexane/ether=9:1)

Sources & evidence

ORD record
ord-1f4f9f8c1029405c9aba3b1bfed4b438
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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