Toluene → 8-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 1095243ノート

反応式

HRID 1095243 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2(O)[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:17][CH2:16][C:11]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 18787929HCID 18787929、化合物

生成物 1

HCID 187879328-(3-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene収率 100.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
30 °C

実験手順

The compound (16) (74.6 g), p-toluenesulfonic acid (2.24 g) and toluene (350 ml) were mixed, and the mixture was heated under reflux for 3 hours while water being distilled was removed. The reaction mixture was cooled to 30° C., and then water (500 ml) and toluene (150 ml) were added and mixed to it. The mixture was then allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Then, the solvent of the solution was distilled off under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=7:3 by volume) as an eluent and silica gel as a stationary phase powder and dried, giving 69.7 g of 8-(3-fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene (17). The yield based on the compound (14) was 86.8%.

後処理

  1. temperaturethe mixture was heated
  2. distillationdistilled
  3. customwas removed
  4. additionwater (500 ml) and toluene (150 ml) were added
  5. additionmixed to it
  6. customhad separated into two phases
  7. washwashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThen, the solvent of the solution was distilled off under reduced pressure
  10. customthe residue was purified with a fractional operation by means of column chromatography
  11. customsilica gel as a stationary phase powder and dried

出典と根拠

ORDレコード
ord-c760314d71cf41c299e81f54234f70f9
出典データセット
uspto-grants-2012_03
特許番号
US08137583B2

反応ノート

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