تفاعل #166101

ord-28789426881a467095cbe816b9279bf3

معادلة التفاعل

c1ccc(C(c2ccccc2)[C@H]2CO2)cc1
(2S)-2-benzhydryl-oxirane
C=[CH][Mg][Br]
vinylmagnesium bromide
C=CC[C@H](O)C(c1ccccc1)c1ccccc1
CuI
C=CC[C@H](O)C(c1ccccc1)c1ccccc1
(2S)-1,1-diphenyl-pent-4-ene-2-ol
C=CC[C@@H](O)C(c1ccccc1)c1ccccc1
(2R)-1,1-diphenyl-pent-4-ene-2-ol

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

(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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08841464B2uspto-grants-2014_09