Sodium Bicarbonate → 5-Fluoromethyl-2-methoxymethoxymethylpyridine

HRID 1985657노트

반응식

HRID 1985657 반응식
O1CCN(S(F)(F)[F:8])CC1.[CH3:11][O:12][CH2:13][O:14][CH2:15][C:16]1[N:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>ClCCl>[F:8][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][CH2:13][O:12][CH3:11])=[N:21][CH:20]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2733258Morpholinosulfur trifluorideHCID 23626004(6-Methoxymethoxymethylpyridin-3-yl)methanol

생성물 1

HCID 577207075-Fluoromethyl-2-methoxymethoxymethylpyridine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of 70% HF-pyridine complex (0.3 ml) is added to a solution of morpholinosulfur trifluoride (2 ml, 1.63×10−2 mol) in dichloromethane (32 ml) cooled to −78° C. and maintained under an inert atmosphere, followed by dropwise addition of 1 g (5.4 mmol) of compound (3) as a solution in CH2Cl2 (10 ml). The mixture is stirred for 2 hours at −78° C. and then poured into saturated NaHCO3 solution (75 ml). The aqueous phase is extracted with dichloromethane and the combined organic phases are washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue is bulb-to-bulb distilled (P: 4.7×10−2 mb, b.p.: 110-130° C.). The title compound is isolated in the form of a colorless oil (0.3 g), which is used directly in the following step.

후처리

  1. temperaturemaintained under an inert atmosphere
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. washthe combined organic phases are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. distillationdistilled (P: 4.7×10−2 mb, b.p.: 110-130° C.)

출처 및 근거

ORD 기록
ord-328505ba22d441858fe268eb962da443
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547700B2

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