Triethylsilane → (4-{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)(triisopropyl)silane

HRID 1836554Notes

Reaction equation

HRID 1836554 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:19][C:18]=2[CH3:35])O)=[CH:11][C:10]=1[S:36]([C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)(=[O:38])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([O:24][Si:25]([CH:26]([CH3:28])[CH3:27])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:30])[CH3:31])=[CH:19][C:18]=2[CH3:35])=[CH:11][C:10]=1[S:36]([C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)(=[O:37])=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 25517Ammonium ChlorideHCID 65367Trimethylsilyl triflateHCID 23499595{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}{2,6-dimethyl-4-[(triisopropylsilyl)oxy]phenyl}methanol

Product 1

HCID 23499604(4-{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)(triisopropyl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

575 mg (0.89 mmol) of {4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]phenyl}{2,6-dimethyl-4-[(triisopropylsilyl)oxy]phenyl}methanol (Example VIII) are dissolved in 10 ml of tetrahydrofuran. At 0° C., 1030.35 mg (8.86 mmol) of triethylsilane are initially added, and 78.78 mg (0.35 mmol) of trimethylsilyl trifluoromethane-sulphonate are then added dropwise. The reaction mixture is stirred for 1.5 hours, and saturated ammonium chloride solution is then added. The mixture is extracted three times with ethyl acetate, the combined organic phases are dried over sodium sulphate and the solvent is removed under reduced pressure. This gives 611 mg (53% of theory) of (4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)(triisopropyl)silane.

Workup

  1. extractionThe mixture is extracted three times with ethyl acetate
  2. dry with materialthe combined organic phases are dried over sodium sulphate
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-cf21c4ac4f5f41409caa839dd7674093
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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