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Water → 2-Methyl-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrile

HRID 2247751
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HRID 2247751 반응식
CS([C:5]1[N:12]=[C:11]([CH2:13][O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])(=O)=O.[CH3:25][Mg]Br.[Cl-].[NH4+].O>CCOCC>[CH3:25][C:5]1[N:12]=[C:11]([CH2:13][O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 685269612-(Methylsulfonyl)-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrileHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 685253732-Methyl-6-(((triisopropylsilyl)oxy)methyl)nicotinonitrile수율 95%

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매
2회

실험 절차

To a solution of 2-(methylsulfonyl)-6-{[(triisopropylsilyl)oxy]methyl}nicotinonitrile (0.80 g, 2.2 mmol) that was obtained in Example 24 (24b) in ether (10 ml) was added a 3.0 M solution of methylmagnesium bromide in ether (1.5 ml, 4.4 mmol) at −78° C. with stirring, and the resulting mixture was stirred at the same temperature for 1 hour. After stirring, a saturated aqueous solution of ammonium chloride (1 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was poured into water (20 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 1:9) as the eluent to afford the title compound (0.64 g) in a yield of 95% as a white crystalline solid.

후처리

  1. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. extractionextracted with ether
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtration
  9. customthe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-182a82e7678742a6ad797f2289075355
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07687491B2

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