Ethyl 4-pentenoate → Ethyl (4E)-5-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)pent-4-enoate

HRID 1920788Notes

Reaction equation

HRID 1920788 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][CH2:11][C@H:12]1[CH2:14][O:13]1)[CH3:9].[C:15]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:16][CH2:17][CH:18]=[CH2:19]>>[O:13]1[CH2:14][C@@H:12]1[CH2:11][O:10][C@@H:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1/[CH:19]=[CH:18]/[CH2:17][CH2:16][C:15]([O:21][CH2:22][CH3:23])=[O:20])[CH3:9]

Participants

3

Reactant 2

HCID 74786Ethyl 4-pentenoateHCID 58981243(2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxirane

Product 1

HCID 58572679Ethyl (4E)-5-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)pent-4-enoateYield 82%

Procedure

By using (2R)-2-{[(1R)-1-(2-bromo phenyl)ethoxy]methyl}oxirane described in WO 2004/094362 and ethyl pent-4-enoate, the reaction was carried out in the same manner as the method described in Example 3 (3c) to give the title compound as a colorless oily substance (yield 82%).

Sources & evidence

ORD record
ord-95dad8623f9243a1ae082de36aaad6cc
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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