Methyl iodide → 2-[3-(Tert-butyldimethylsilanyloxy)-4,4,4-trifluoro 1-methylbutyl]pyridine

HRID 1988156노트

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HRID 1988156 반응식
[Si:1]([O:8][CH:9]([C:18]([F:21])([F:20])[F:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[CH3:23]C([N-]C(C)C)C.CI>C1COCC1>[Si:1]([O:8][CH:9]([C:18]([F:19])([F:21])[F:20])[CH2:10][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 223986342-[3-(Tert-butyldimethylsilanyloxy)-4,4,4-trifluorobutyl]pyridine

생성물 1

HCID 223986112-[3-(Tert-butyldimethylsilanyloxy)-4,4,4-trifluoro 1-methylbutyl]pyridine수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-75 °C

실험 절차

A solution of 810 mg (2.54 mmol) of 2-[3-(tert-butyldimethylsilanyloxy)-4,4,4-trifluorobutyl]pyridine in 8 nL of THF was treated with 2.54 mL (3.81 mmol, 1.5 eq.) of LDA (1.5 M solution in cyclohexane) at −75° C. After stirring at −75° C. for 45 minutes, 474 μL (7.61 mmol, 3.0 eq.) of methyl iodide was added at −75° C. The resulting mixture was stirred at this temperature for 10 minutes and quenched with saturated NH4Cl solution. The product was extracted into ether. The ethereal layer was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give 750 mg (89%) of 2-[3-(tert-butyldimethylsilanyloxy)-4,4,4-trifluoro-1-methylbutyl]pyridine (a mixture of two diastereomers) as a brown oil.

후처리

  1. stirringThe resulting mixture was stirred at this temperature for 10 minutes
  2. customquenched with saturated NH4Cl solution
  3. extractionThe product was extracted into ether
  4. washThe ethereal layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-abae87a1b6f54688a73172febba1cda2
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553966B2

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