Triethyl 2-fluoro-2-phosphonoacetate → (E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-pent-2-enoic acid ethyl ester
Reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].[CH2:16]([N:18]1[C:27]2[C:22](=[CH:23][C:24]([CH:32]([CH3:34])[CH3:33])=[CH:25][C:26]=2[C:28](=O)[CH2:29][CH3:30])[C:21]([CH3:36])([CH3:35])[CH2:20][CH2:19]1)[CH3:17]>>[CH2:2]([O:3][C:4](=[O:5])/[C:6](/[F:7])=[C:28](\[C:26]1[CH:25]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:23]=[C:22]2[C:27]=1[N:18]([CH2:16][CH3:17])[CH2:19][CH2:20][C:21]2([CH3:35])[CH3:36])/[CH2:29][CH3:30])[CH3:1]Participants
3
Procedure
Following General Procedure E, triethyl-2-fluoro-2-phosphonoacetate (15.1 g, 62.3 mmol) and 1-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-1-propanone (Intermediate 13, 4.48 g, 15.6 mmol) were reacted to give the title compound as bright yellow oil after purification by flash chromatography (SiO2, 2:98 ethyl acetate:hexane).