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

HRID 78917ノート

反応式

HRID 78917 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 11816639(2S)-2-(Diphenylmethyl)oxirane収率 77.5%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1cdf6805acd84de2ab43cd3648b16dfd
出典データセット
uspto-grants-2014_09
特許番号
US08841464B2

反応ノート

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