Sodium Bicarbonate → 5-Fluoromethyl-2-methoxymethoxymethylpyridine

HRID 1985657ノート

反応式

HRID 1985657 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 577207075-Fluoromethyl-2-methoxymethoxymethylpyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-328505ba22d441858fe268eb962da443
出典データセット
uspto-grants-2009_06
特許番号
US07547700B2

反応ノート

読み込み中…