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

HRID 83105

反応式

HRID 83105 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
57.5 °C

実験手順

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%).

後処理

  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))

出典と根拠

ORDレコード
ord-ad24439d2b614dd9810ed68150b04d5c
出典データセット
uspto-grants-2014_09
特許番号
US08846749B2

関連ノート

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