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

HRID 28466

반응식

HRID 28466 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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 eluent 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)−.

후처리

  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 eluent

출처 및 근거

ORD 기록
ord-b316e528be8a433d9b5f0376e798d03e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419986B2

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