Epithiochlorohydrin → 11-hydroxy-9-(thiiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one

HRID 83105

반응식

HRID 83105 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]([OH:16])[CH:15]=1)[C:12](=[O:17])[C:11]1[C:6](=[CH:7][CH:8]=[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]3=1)[O:5]2.[CH2:22]1[S:24][CH:23]1[CH2:25]Cl>CC(C)=O>[OH:16][C:14]1[CH:15]=[C:2]([O:1][CH2:25][CH:23]2[CH2:22][S:24]2)[CH:3]=[C:4]2[C:13]=1[C:12](=[O:17])[C:11]1[C:6](=[CH:7][CH:8]=[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]3=1)[O:5]2

참가 물질

4

반응물 2

HCID 18588EpithiochlorohydrinHCID 157102119,11-dihydroxy-12H-benzo(a)xanthen-12-one

생성물 1

HCID 4623258311-hydroxy-9-(thiiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one수율 43.3%

시약·촉매·용매 1

HCID 180Acetone용매2회

반응 조건

온도
57.5 °C

실험 절차

9,11-dihydroxy-12H-benzo[a]xanthen-12-one (0.1 g, 0.18 mmol) prepared in Step 1 of Examples 14 and 15, CS2CO3 (0.36 g, 0.54 mmol), and anhydrous acetone (13 mL) were charged to a dry round-bottom flask, and epithiochlorohydrin (0.2 g, 1.08 mmol) dissolved in anhydrous acetone (2 mL) was added thereto with stirring. The reaction mixture was stirred with reflux overnight at a temperature of 55 to 60° C. under a nitrogen atmosphere. Solid of the reaction mixture was filtered, removed and concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give a yellow solid compound 11-hydroxy-9-(thiiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (27.3 mg, 21.7%) and a yellow solid compound 9,11-bis(thiiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (31.2 mg, 20.5%).

후처리

  1. additionwas added
  2. stirringThe reaction mixture was stirred
  3. filtrationSolid of the reaction mixture was filtered
  4. customremoved
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated
  7. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

출처 및 근거

ORD 기록
ord-ad24439d2b614dd9810ed68150b04d5c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846749B2

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