Triethyl 2-fluoro-2-phosphonoacetate → (E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enoic acid ethyl ester

HRID 1582089Notes

Reaction equation

HRID 1582089 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].[CH2:16]([N:19]1[C:28]2[C:23](=[CH:24][C:25]([CH:32]([CH3:34])[CH3:33])=[CH:26][C:27]=2[C:29](=O)[CH3:30])[C:22]([CH3:36])([CH3:35])[CH2:21][CH2:20]1)[CH2:17][CH3:18]>>[CH2:2]([O:3][C:4](=[O:5])/[C:6](/[F:7])=[C:29](\[C:27]1[CH:26]=[C:25]([CH:32]([CH3:34])[CH3:33])[CH:24]=[C:23]2[C:28]=1[N:19]([CH2:16][CH2:17][CH3:18])[CH2:20][CH2:21][C:22]2([CH3:35])[CH3:36])/[CH3:30])[CH3:1]

Participants

3

Reactant 2

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 227198321-(6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone2×

Product 1

HCID 69898585(E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enoic acid ethyl ester

Procedure

Following General Procedure E, triethyl-2-fluoro-2-phosphonoacetate (8.36 g, 34.5 mmol) and 1-(1-n-propyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone (Intermediate 14, 2.78 g, 9.86 mmol) were reacted to give the title compound as a yellow oil after purification by flash chromatography (SiO2, 2:98 ethyl acetate:hexane).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-79a7c7758be64d0d96aa01cd16414052
Source dataset
uspto-grants-2004_05
Patent number
US06734193B1

Reaction notes

Loading…