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

HRID 1826663Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 50 °C

Procedure

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. The reaction mixture was cooled to ambient temperature, triethylamine (0.5 mL) was added to the reaction mixture, 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).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customthe solvent was removed under reduced pressure
customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1)

Sources & evidence

ORD record: ord-903c13ac66614d2faa304d6bd441110a
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053060B2

Reaction notes

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