Methyl 4-fluorobenzoylacetate → HCID 86658322, compound

HRID 1890270Notes

Reaction equation

HRID 1890270 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Cl-].[CH3:16][CH:17]1[CH2:21][CH2:20][C:19](=[O:22])[N:18]1[NH3+:23]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:23][N:18]2[C:19](=[O:22])[CH2:20][CH2:21][CH:17]2[CH3:16])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 579425Methyl 4-fluorobenzoylacetateHCID 67437276HCID 67437276, compound

Product 1

HCID 86658322HCID 86658322, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 7.50 g (38.2 mmol) of methyl 3-(4-fluorophenyl)-3-oxopropanoate and 11.5 g (76.5 mmol) of 2-methyl-5-oxopyrrolidin-1-aminium chloride in 50 ml of pyridine is stirred at room temperature for 72 h. The reaction mixture is concentrated under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 10.4 g (93%) of the desired product as a mixture of isomers; log P(HCOOH): 2.13 and 2.45; 1H-NMR (ppm): δ (DMSO-d6)=1.16-1.19 (m, 3H), 1.58-1.62 (m, 2H), 2.20-2.22 (m, 1H), 2.36-2.41 (m, 1H), 3.54 (s, 2.25H), 3.64 (s, 0.75H), 3.80 (d, 1H), 3.90 (d, 1H), 3.80 (q, 1H), 7.24 (t, 0.6H), 7.29 (t, 1.4H), 7.44-7.47 (m, 0.6H), 7.89-7.92 (m, 1.4H); LC-MS: m/z=293 [M+H]+.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customPurification by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-8588c0f702404ffb8dedc474e606fe99
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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