Epichlorohydrin → 1,3-bis(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one

HRID 83110

反応式

HRID 83110 の反応式
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>CC(C)=O>[O:26]1[CH2:25][CH:24]1[CH2:22][O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([O:21][CH2:22][CH:24]2[CH2:25][O:26]2)[CH:3]=1

参加物

4

反応物 2

HCID 7835EpichlorohydrinHCID 107077051,3-dihydroxy-12H-benzo(b)xanthen-12-one

生成物 1

HCID 462326481,3-bis(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one収率 21.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
57.5 °C

実験手順

1,3-dihydroxy-12H-benzo[b]xanthen-12-one (0.15 g, 0.54 mmol) synthesized in Step 1 of Example 18, CS2CO3 (0.53 g, 1.62 mmol), and anhydrous acetone (30 mL) were charged to a dry round-bottom flask, and epichlorohydrin (0.25 g, 2.7 mmol) was added thereto with stirring using a syringe. The reaction mixture was stirred with reflux under a nitrogen atmosphere (55 to 60° C., overnight). Solid of the reaction mixture was filtered and removed, and the filtrate was 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 the title compound (15.3 mg, 21.8%) as a yellow solid.

後処理

  1. stirringThe reaction mixture was stirred
  2. filtrationSolid of the reaction mixture was filtered
  3. customremoved
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was separated
  6. 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-1d03c9ea32d24eaebcef6e626a5f8f1c
出典データセット
uspto-grants-2014_09
特許番号
US08846749B2

関連ノート

読み込み中…