Ammonium Chloride → 1-Hydroxy-1-(3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane

HRID 1174444ノート

反応式

HRID 1174444 の反応式
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH3:10].[Mg].[CH2:13]([CH:16]1[CH2:21][CH2:20][CH:19]([CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]=[O:30])[CH2:24][CH2:23]2)[CH2:18][CH2:17]1)[CH2:14][CH3:15].[Cl-].[NH4+]>C1COCC1>[OH:30][CH:29]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH3:10])=[C:2]([F:1])[CH:3]=1)[CH2:28][CH:25]1[CH2:26][CH2:27][CH:22]([CH:19]2[CH2:20][CH2:21][CH:16]([CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18]2)[CH2:23][CH2:24]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 13999102trans-4-(trans-4-Propylcyclohexyl)cyclohexylacetaldehydeHCID 145169324-Bromo-1-ethoxy-2-fluorobenzene

生成物 1

HCID 231596811-Hydroxy-1-(3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane収率 96.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

30 ml of a THF solution of 15.0 g (68.5 mmol) of 3-fluoro-4-ethoxybromobenzene was dropped under stirring to 1.8 g (75.4 mmol) of dried turnings magnesium at 40 to 60° C. Then, 100 ml of a THF solution of 22.3 g (89.1 mmol) of (4-(4-propylcyclohexyl)cyclohexyl)acetoaldehyde was dropped to the solution and stirred for 2 hours. The reaction mixture was poured into 100 ml of an aqueous saturated ammonium chloride solution and extracted with 200 ml of toluene. The organic layer was washed with 100 ml of water and then with 100 ml of aqueous saturated sodium chloride solution successively and, after drying over anhydrous magnesium sulfate, concentrated under a reduced pressure to obtain 25.9 g of crude 1-hydroxy-1-(3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane.

後処理

  1. extractionextracted with 200 ml of toluene
  2. washThe organic layer was washed with 100 ml of water
  3. dry with materialwith 100 ml of aqueous saturated sodium chloride solution successively and, after drying over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure

出典と根拠

ORDレコード
ord-911447be88d44f98a7adb2d7f6386703
出典データセット
uspto-grants-2010_11
特許番号
US07838087B2

反応ノート

読み込み中…