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

HRID 909735노트

반응식

HRID 909735 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e627dff4bbdc4cf4b364b7c8b9224429
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017791B2

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