Triethylamine → 2-[4-(2-hydroxyethyl)benzyl]-5-methoxyphenyl beta-D-glucopyranoside

HRID 1982853ノート

反応式

HRID 1982853 の反応式
[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][O:30]COC)=[CH:24][CH:23]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO>[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][OH:30])=[CH:26][CH:27]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 688708525-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl beta-D-glucopyranoside

生成物 1

HCID 688718222-[4-(2-hydroxyethyl)benzyl]-5-methoxyphenyl beta-D-glucopyranoside収率 47.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of 5-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl β-D-glucopyranoside (0.053 g) in methanol (2.3 mL) was added p-toluenesulfonic acid monohydrate (0.032 g), and the mixture was stirred at 50° C. for 3 hours. After cooling to room temperature, to the reaction mixture was added triethylamine (0.5 mL), and the solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give 2-[4-(2-hydroxyethyl)-benzyl]-5-methoxyphenyl β-D-glucopyranoside (0.023 g).

後処理

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1)

出典と根拠

ORDレコード
ord-ca0e9f45270846bc84ad26ae212bd657
出典データセット
uspto-grants-2009_06
特許番号
US07541341B2

反応ノート

読み込み中…