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

HRID 909737ノート

反応式

HRID 909737 の反応式
C([C@H]1CO1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Mg]Br)=C.[C:21]1([CH:27]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:28]([OH:32])[CH2:29][CH:30]=[CH2:31])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:33]1([CH:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:28]([OH:32])[CH2:29][CH:30]=[CH2:31])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

参加物

4

反応物 3

HCID 11390776(2S)-1,1-diphenyl-pent-4-ene-2-olHCID 11816639(2S)-2-(Diphenylmethyl)oxiraneHCID 178418507HCID 178418507、化合物

生成物 1

HCID 11299399(2R)-1,1-diphenyl-pent-4-ene-2-ol収率 694.5%

実験手順

(2S)-2-benzhydryl-oxirane (0.61 g, 2.91 mmol) was reacted with vinylmagnesium bromide (7.26 ml of 1.0M solution in THF, 7.26 mmol) in the presence of CuI (0.055 g, 0.29 mmol) (Procedure A) to yield (2R)-1,1-diphenyl-pent-4-ene-2-ol 0.48 g (70%, [α]D=(+)26, c=1, MeOH). The 1HNMR and 13CNMR were identical with (2S)-1,1-diphenyl-pent-4-ene-2-ol.

出典と根拠

ORDレコード
ord-979c82f3bbd34f37902c441e084268a2
出典データセット
uspto-grants-2011_09
特許番号
US08017791B2

反応ノート

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