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

HRID 1174444노트

반응식

HRID 1174444 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-911447be88d44f98a7adb2d7f6386703
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838087B2

반응 노트

불러오는 중…