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

HRID 78919ノート

反応式

HRID 78919 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-28789426881a467095cbe816b9279bf3
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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