Ammonium Chloride → 8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1454779

反応式

HRID 1454779 の反応式
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].[Mg].[O:12]1[C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1.[Cl-].[NH4+]>O1CCCC1>[F:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[C:19]1([OH:22])[CH2:20][CH2:21][C:16]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:17][CH2:18]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 675971-Bromo-2,4,5-trifluorobenzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

生成物 1

HCID 574243598-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
50 °C

実験手順

A three neck flask (2 L) under an atmosphere of nitrogen with Mg turnings (9.8 g) was stirred for 15 rain and tetrahydrofuran (90 m1L) was added and stirring continued for an additional 15 min. 1-Bromo-2,4,5-trifluorobenzene (85 g) was dissolved in tetrahydrofuran (340 mL). A portion of this solution (75 mL) was added to the stirred magnesium turnings and then heated to 50° C. The rest of the solution was added and stirring continued at the same temperature for an additional 1 h. The reaction mixture was cooled to 40° C., a solution of 1,4-dioxaspiro[4.5]decan-8-one (57.3 g) in tetrahydrofuran (275 mL) was added, and stirring continued for 10 h. The reaction mixture was poured into saturated aqueous ammonium chloride solution (970 mL) and extracted with toluene (700 mL). The organic layer was washed with water (3×700 mL), dried over anhydrous sodium sulfate, filtered and evaporated to yield the title compound as a red-orange oil which was used in the next step without further purification.

後処理

  1. additionwas added
  2. additionThe rest of the solution was added
  3. stirringstirring
  4. waitcontinued at the same temperature for an additional 1 h
  5. temperatureThe reaction mixture was cooled to 40° C.
  6. stirringstirring
  7. waitcontinued for 10 h
  8. extractionextracted with toluene (700 mL)
  9. washThe organic layer was washed with water (3×700 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customevaporated

出典と根拠

ORDレコード
ord-2a34ede49fac455695b60becdf019411
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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