Hydrochloric Acid → HCID 23103563, compound

HRID 230877Notes

Reaction equation

HRID 230877 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([OH:25])[C:12]([C:13](=O)[CH:14]=[CH:15][CH:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH2:17]2)=[C:11]([O:26][CH2:27]C(OC)=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([OH:25])[C:12]2[C:13]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:27][O:26][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 67136322HCID 67136322, compound

Product 1

HCID 23103563HCID 23103563, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4′-benzyloxy-6′-hydroxy-2′-(methoxycarbonylmethoxy)dihydrochalcone (0.53 g) in methanol (10 mL) was added sodium methoxide (28% methanol solution, 0.72 mL), and the mixture was heated for reflux overnight. The reaction mixture was cooled to room temperature and acidified by addition of 1 mol/L hydrochloric acid. The resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1-3/1) to give 6-benzyloxy-4-hydroxy-3-(2-phenylethyl)benzofuran (98 mg). This material was dissolved in dichloromethane (5 mL). To the solution were added 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.42 g) and boron trifluoride-diethyl ether complex (0.11 mL) successively, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-benzyloxy-3-(2-phenylethyl)benzofuran (0.19 g). This material was dissolved in tetrahydrofuran (5 mL). To the solution was added 10% palladium-carbon powder (21 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 1.5 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethylacetate=2/1-3/2-1/1) to give the title compound (70 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperaturefor reflux overnight
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1-3/1)

Sources & evidence

ORD record
ord-ec3af9eacbc84715832aa613280975e1
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

Loading…