Methyl iodide → 3-[Methoxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

HRID 1161073Notes

Reaction equation

HRID 1161073 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].O1CCC[CH2:30]1.[H-].[Na+].IC>C(=O)([O-])O.[Na+]>[CH3:30][O:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:20]([CH3:21])[CH3:22])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 666996123-[Hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

Product 1

HCID 666995633-[Methoxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-[hydroxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile (0.64 g, 1.62 mmol) and tetrahydrofuran (10 mL) is stirred at 0° C. Sodium hydride, 60% in mineral oil, (80 mg, 1.95 mmol) is added and the mixture is stirred at room temperature 10 min. The mixture is cooled to 0° C. and iodomethane (0.12 mL, 1.8 mmol) is added. The resulting mixture is stirred at room temperature 18 hr. The mixture is diluted with aqueous saturated sodium hydrogen carbonate, extracted with ethyl acetate, and the organic layer concentrated. The residue is purified via silica chromatography eluting with hexanes to 9:1 hexanes:ethyl acetate to provide 400 mg, 60% the title compound, as a colorless oil. 1H NMR (CDC13) δ 7.70 (s, 1H), 7.55-7.69 (m, 2H), 7.27-7.46 (m, 5H), 5.27 (s, 1H), 4.88 (s, 2H), 3.41 (s, 3H), 1.05-1.29 (m, 21H).

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. stirringThe resulting mixture is stirred at room temperature 18 hr
  3. extractionextracted with ethyl acetate
  4. concentrationthe organic layer concentrated
  5. customThe residue is purified via silica chromatography
  6. washeluting with hexanes to 9:1 hexanes

Sources & evidence

ORD record
ord-fbc16c6d4d764ef186129a68057e6ce7
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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