Triphenylphosphine → 3-Acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester

HRID 1422912ノート

反応式

HRID 1422912 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[C:13]=2[F:15])[N:8]=[CH:7][C:6]=1[O:17][C:18](=[O:20])[CH3:19])=[O:4].[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CO.ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH3:21])[C:13]=2[F:15])[N:8]=[CH:7][C:6]=1[O:17][C:18](=[O:20])[CH3:19])=[O:4]

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 672473533-Acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester

生成物 1

HCID 672479353-Acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester収率 65.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methanol (0.52 mL, 12.72 mmol, 3.0 eq) is added at room temperature to a stirred solution of 3-acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester (1.18 g, 4.24 mmol, 1.0 eq) in tetrahydrofuran (50 mL), followed by triphenylphosphine (2.22 g, 12.72 mmol, 3.0 eq) and diethyl azodicarboxylate (1.48 g, 12.72 mmol, 3.0 eq). After 3 hours stirring at room temperature, solvent is evaporated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 30:1, v/v) to afford 3-acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester as a yellow oil (0.81 g, 65% yield).

後処理

  1. customsolvent is evaporated
  2. customto give a crude product that
  3. customis purified by column chromatography (silica gel, eluent

出典と根拠

ORDレコード
ord-1adfdf1fdb8c4b6683baf0cc579169ef
出典データセット
uspto-grants-2015_01
特許番号
US08927541B2

反応ノート

読み込み中…