Gallacetophenone → 5-Hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl-1-ethanone

HRID 1267869Notes

Reaction equation

[OH:1][C:2]1[C:7]([OH:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)([O:22][CH2:23][C@@H:24]1O[CH2:25]1)(=O)=O>CN(C=O)C>[OH:1][C:2]1[C:7]2[O:8][CH:24]([CH2:23][OH:22])[CH2:25][O:9][C:6]=2[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2′,3′,4′-trihydroxyacetophenone (10.6 g, 63.0 mmole) in DMF (75 mL) was added potassium carbonate (17.4 g, 126 mmole). After 5 minutes (R)-glycidyl tosylate (9.67 g, 42,3 mmole) was added then the heterogeneous mixture was heated to 70° C. for 3 hours. After removal of the solvent in vacuum, the residue was taken into water (800 mL) and was then extracted with ethyl acetate (4×300 mL). The combined organic layers were dried over MgSO4, filtered and evaporate to dryness in vacuum. The crude brown oil thus obtained was column chromatographed on silica gel with 40% hexane/ethyl acetate as eluant to give the (S)-enantiomer of the title compound as a yellow oil which solidifies upon standing (7.5 g, 78%). MS (ESI) m/z 223 (M−H)−.

Workup

customAfter removal of the solvent in vacuum
extractionwas then extracted with ethyl acetate (4×300 mL)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
customevaporate to dryness in vacuum
customThe crude brown oil thus obtained
customchromatographed on silica gel with 40% hexane/ethyl acetate as eluant

Sources & evidence

ORD record: ord-9aecadf7bd9047a0911a97f31567734e
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555560B2

Reaction notes

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