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

HRID 1836553ノート

反応式

HRID 1836553 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bdab0eda3d9040d5bffdb2d5aaced051
出典データセット
uspto-grants-2004_08
特許番号
US06777442B2

反応ノート

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