Sodium Methoxide → HCID 9909814, compound

HRID 230878Notes

Reaction equation

HRID 230878 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:30]2[C:31]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][O:33][C:29]=2[CH:28]=[C:27]([OH:42])[CH:26]=1)(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([O:24][C:25]2[C:30]3[C:31]([CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:32][O:33][C:29]=3[CH:28]=[C:27]([OH:42])[CH:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67135831HCID 67135831, compound

Product 1

HCID 9909814HCID 9909814, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-hydroxy-3-(2-phenylethyl)benzofuran (45 mg) in methanol (3 mL) was added sodium methoxide (28% methanol solution, 0.015 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under deduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (28 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under deduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1)

Sources & evidence

ORD record
ord-5c835998b0e14edab6a9100cc5fb9925
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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