Sodium Hydroxide → 8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 1454780

反応式

HRID 1454780 の反応式
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[C:22]1(O)[CH2:31][CH2:30][C:25]2([O:29][CH2:28][CH2:27][O:26]2)[CH2:24][CH2:23]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[C:22]1[CH2:31][CH2:30][C:25]2([O:26][CH2:27][CH2:28][O:29]2)[CH2:24][CH:23]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrate2 回HCID 574243598-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

生成物 1

HCID 574243608-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a round-bottomed flask (3 L) under nitrogen atmosphere equipped with a Dean-Stark trap, toluene (350 mL), para-toluenesulphonic acid monohydrate (p-TSA) (1 g) and 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (94.2 g) were added and the mixture was refluxed overnight. Additional p-TSA (1 g) was added. Refluxing was continued overnight and then the reaction was stirred at room temperature for two more days. The reaction mixture was treated with 0.1 N aqueous sodium hydroxide solution (500 mL) and extracted with heptanes (500 m-L). The organic layer was washed with water (3×500 mL), dried over anhydrous sodium sulfate, filtered and evaporated to yield crude product which was purified by column chromatography (silica gel, gradient 2% to 40% ethyl acetate in heptanes) to yield the title compound.

後処理

  1. additionwere added
  2. temperaturethe mixture was refluxed overnight
  3. temperatureRefluxing
  4. extractionextracted with heptanes (500 m-L)
  5. washThe organic layer was washed with water (3×500 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto yield crude product which
  10. customwas purified by column chromatography (silica gel, gradient 2% to 40% ethyl acetate in heptanes)

出典と根拠

ORDレコード
ord-0ce8d6623e3b42ecb71a21c146ccdded
出典データセット
uspto-grants-2009_01
特許番号
US07482336B2

関連ノート

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