Methyl 3-butenoate → Methyl (3E)-4-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)but-3-enoate
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].[CH3:15][O:16][C:17](=[O:21])[CH2:18][CH:19]=[CH2:20]>>[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:20]=[CH:19]/[CH2:18][C:17]([O:16][CH3:15])=[O:21])[CH3:9]Participants
3
Procedure
By using (2R)-2-{[(1R)-1-(2-bromo phenyl)ethoxy]methyl}oxirane (257 mg, 1.00 mmol) described in WO 2004/094362 and methylbut-3-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 yellow oily substance (yield 65%).
Sources & evidence
- ORD record
- ord-e339da1dd5744781bfeabef91d7d4322
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173631B2
Reaction notes
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