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

HRID 606994Notes

Reaction equation

HRID 606994 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

(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.

Sources & evidence

ORD record
ord-7a534fa8278b41e5b9aa35ec05b9129f
Source dataset
uspto-grants-2011_03
Patent number
US07915433B2

Reaction notes

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