Methyl 4-fluorobenzoylacetate → HCID 86658322、化合物

HRID 1890270ノート

反応式

HRID 1890270 の反応式
[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

参加物

4

反応物 2

HCID 579425Methyl 4-fluorobenzoylacetateHCID 67437276HCID 67437276、化合物

生成物 1

HCID 86658322HCID 86658322、化合物収率 93.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-8588c0f702404ffb8dedc474e606fe99
出典データセット
uspto-grants-2013_08
特許番号
US08507472B2

反応ノート

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