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

HRID 495407ノート

反応式

HRID 495407 の反応式
[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]

参加物

5

反応物 3

HCID 10706GallacetophenoneHCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-

生成物 1

HCID 218920935-Hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl-1-ethanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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 magnesium sulfate, 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)−.

後処理

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

出典と根拠

ORDレコード
ord-21776709f92d4c01be3f53c2cec2dd31
出典データセット
uspto-grants-2005_09
特許番号
US06939877B2

反応ノート

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