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

HRID 1717760노트

반응식

HRID 1717760 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

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 (CDCl3) 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).

후처리

  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

출처 및 근거

ORD 기록
ord-22342fda843349b4bf11a3f29a86d260
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803938B2

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