Ammonium Chloride → {4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}{2,6-dimethyl-4-[(triisopropylsilyl)oxy]phenyl}methanol

HRID 1836553노트

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HRID 1836553 반응식
[CH:1]([Si:4]([O:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15](Br)=[C:14]([CH3:20])[CH:13]=1)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C([Li])CCC.[CH2:26]([O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[O:39])=[CH:36][C:35]=1[S:42]([C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=1)(=[O:44])=[O:43])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:26]([O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]([C:15]2[C:16]([CH3:18])=[CH:17][C:12]([O:11][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])=[CH:13][C:14]=2[CH3:20])[OH:39])=[CH:36][C:35]=1[S:42]([C:45]1[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=1)(=[O:44])=[O:43])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 22605990(4-Bromo-3,5-dimethyl-phenoxy)triisopropylsilaneHCID 234995924-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 23499595{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}{2,6-dimethyl-4-[(triisopropylsilyl)oxy]phenyl}methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

810 mg (2.27 mmol) of 4-bromo-3,5-dimethylphenyl triisopropylsilyl ether (Example VII) are dissolved in 10 ml of tetrahydrofuran. At −78° C., 147.3 mg (2.3 mmol) of butyllithium (2.4 molar in hexane) are added dropwise. At the same temperature, stirring is continued for one hour, and 600 mg (1.62 mmol) of 4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzaldehyde (Example VI), dissolved in 4 ml of tetrahydrofuran, are then added dropwise. The mixture is stirred at −78° C. for one hour, and saturated ammonium chloride solution is then added. The mixture is extracted three times with ethyl acetate and the combined organic phases are dried with sodium sulphate and concentrated. This gives 580 mg (55% of theory) of {4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}{2,6-dimethyl-4-(triisopropylsilyl)oxy]phenyl}methanol.

후처리

  1. additionare then added dropwise
  2. stirringThe mixture is stirred at −78° C. for one hour
  3. extractionThe mixture is extracted three times with ethyl acetate
  4. dry with materialthe combined organic phases are dried with sodium sulphate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bdab0eda3d9040d5bffdb2d5aaced051
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777442B2

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