Ammonium Chloride → HCID 23499595, compound

HRID 1836553Notes

Reaction equation

HRID 1836553 reaction equation
[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

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 22605990(4-Bromo-3,5-dimethyl-phenoxy)triisopropylsilaneHCID 23499592HCID 23499592, compoundHCID 178418339Butyllithium

Product 1

HCID 23499595HCID 23499595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bdab0eda3d9040d5bffdb2d5aaced051
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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