Water → Methyl 3-methoxy-5-(3-methoxypropoxy)benzoate

HRID 1698355ノート

反応式

HRID 1698355 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH3:12])[CH:5]=1.[CH3:14][O:15][CH2:16][CH2:17]COS(C1C=CC(C)=CC=1)(=O)=O.[C:30]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[C:6]([O:11][CH2:12][CH2:17][CH2:16][O:15][CH3:14])[CH:7]=[C:8]([O:10][CH3:30])[CH:9]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 135229883-Methoxypropyl 4-methylbenzenesulfonateHCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

生成物 1

HCID 59817706Methyl 3-methoxy-5-(3-methoxypropoxy)benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 3-methoxy-5-hydroxybenzoic acid methyl ester (23.2 g, 127 mmol), toluene-4-sulfonic acid 3-methoxy-propyl ester (40.7 g, 167 mmol) and Kl (2.23 g, 13.4 mmol) in DMF (350 mL), K2CO3 (53.1 g, 384 mmol) is added under N2. After stirring at 60° C. for 17 h, the reaction mixture is supplemented with H2O and extracted with Et2O. The combined organic phases are washed with H2O and dried (Na2SO4). Concentration under reduced pressure and silica gel flash chromatography give the title compound as colorless oil. MS: 255 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 3.80 min.

後処理

  1. extractionextracted with Et2O
  2. washThe combined organic phases are washed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration under reduced pressure and silica gel flash chromatography

出典と根拠

ORDレコード
ord-56802f60222348b68277d2f96277ad75
出典データセット
uspto-grants-2012_04
特許番号
US08163773B2

反応ノート

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