Methyl iodide → tert-Butyl-[4-(4-chloro-phenyl)-4-methoxy-butoxy]-diphenyl-silane

HRID 1643307Notes

Reaction equation

HRID 1643307 reaction equation
[H-].[Na+].[C:3]([Si:7]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[OH:13])([CH3:6])([CH3:5])[CH3:4].[CH3:33]I>C1COCC1>[C:3]([Si:7]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[O:13][CH3:33])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 595688264-(tert-Butyl-diphenyl-silanyloxy)-1-(4-chloro-phenyl)-butan-1-ol

Product 1

HCID 59568823tert-Butyl-[4-(4-chloro-phenyl)-4-methoxy-butoxy]-diphenyl-silaneYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (153 mg 60% dispersed in mineral oil, 6.39 mmol) in 20 mL THF was slowly added at room temperature 4-(tert-butyl-diphenyl-silanyloxy)-1-(4-chloro-phenyl)-butan-1-ol (330 mg, 0.75 mmol) as a solution in 10 mL THF followed by the dropwise addition of methyl iodide (339 μL, 5.25 mmol). The reaction mixture was stirred for 3 h at room temperature before being quenched by the careful addition of saturated aqueous NH4Cl (30 mL). The mixture was extracted with ethylacetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. After evaporation of solvent the product was isolated by flash column chromatography eluting with 0% to 30% ethyl acetate/hexane to give 343 mg of the title compound as a colorless oil.

Workup

  1. custombefore being quenched by the careful addition of saturated aqueous NH4Cl (30 mL)
  2. extractionThe mixture was extracted with ethylacetate (3×30 mL)
  3. washthe combined organic layers washed with brine (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of solvent the product
  6. customwas isolated by flash column chromatography
  7. washeluting with 0% to 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-53a9dc3559c54d7c81f5529a4653033c
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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