Ammonium Chloride → 1-(4-Ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol

HRID 1464847ノート

反応式

HRID 1464847 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[C:4]([F:11])[C:3]=1[F:12].C([Li])CCC.[CH2:18]([CH:21]1[CH2:25][CH2:24][CH:23]([CH:26]2[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]2)[CH2:22]1)[CH2:19][CH3:20].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([C:29]2([OH:32])[CH2:28][CH2:27][CH:26]([CH:23]3[CH2:24][CH2:25][CH:21]([CH2:18][CH2:19][CH3:20])[CH2:22]3)[CH2:31][CH2:30]2)=[C:3]([F:12])[C:4]=1[F:11])[CH3:10]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 269854911-Bromo-4-ethoxy-2,3-difluorobenzeneHCID 679922824-(3-Propylcyclopentyl)-cyclohexanoneHCID 178418339Butyllithium

生成物 1

HCID 679923521-(4-Ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol収率 94.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

THF (100 ml) was added to 1-bromo-4-ethoxy-2,3-difluorobenzene (5.1 g) in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to −78° C. n-Butyllithium (1.57 M, in a hexane solution) (13.8 ml) was added dropwise at a temperature of −70° C. or lower. The stirring was continued at −78° C. for another 2 hours, and 4-(3-propylcyclopentyl)-cyclohexanone (3.0 g) in a THF (10 ml) solution was added dropwise at a temperature of −70° C. or lower. After the mixture had been stirred at −78° C. for another 1 hour, it was warmed to room temperature, and a saturated aqueous solution of ammonium chloride (50 ml) was added. The mixture was separated, and the water layer was extracted with ethyl acetate three times, and then the combined organic layer was washed with brine. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume) to give 1-(4-ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol (5.0 g).

後処理

  1. temperatureit was warmed to room temperature
  2. customThe mixture was separated
  3. extractionthe water layer was extracted with ethyl acetate three times
  4. washthe combined organic layer was washed with brine
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume)

出典と根拠

ORDレコード
ord-827e5e7f239840f2b27cb68413de5dcc
出典データセット
uspto-grants-2015_04
特許番号
US08999197B2

反応ノート

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