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

HRID 1429037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429037
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 11816639(2S)-2-(Diphenylmethyl)oxiraneAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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 (25)-2-benzhydryl-oxirane 23b 2.5 g (78%, ([α]D=(−)9.6, c=1, MeOH). The 1HNMR and 13CNMR were identical with (R)-isomer.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0d0a9be4b24d4c55bcddfd37c7ab8da9
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937189B2

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