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

HRID 909737노트

반응식

HRID 909737 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

(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.

출처 및 근거

ORD 기록
ord-979c82f3bbd34f37902c441e084268a2
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017791B2

반응 노트

불러오는 중…