Ethyl bromoacetate → Ethyl[(6-chloro-2-methylpyridin-3-yl)methoxy]acetate

HRID 385977노트

반응식

HRID 385977 반응식
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([CH2:11][OH:12])=[CH:6][CH:5]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1.O>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:12][CH2:11][C:7]1[C:8]([CH3:10])=[N:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[CH3:19]

참가 물질

6

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 59525984(6-Chloro-2-methylpyridin-3-yl)methanol

생성물 1

HCID 59526379Ethyl[(6-chloro-2-methylpyridin-3-yl)methoxy]acetate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (266 mg of 60%, 6.66 mol) was suspended in tetrahydrofuran (14.8 mL) and cooled to 0° C. (6-Chloro-2-methylpyridin-3-yl)methanol (Example 421 Step 1) (350 mg, 2.22 mmol) was added and the mixture was stirred for 30 minutes at 0° C. Ethyl bromoacetate (0.25 mL, 2.22 mmol) was added and the solution was heated to 50° C. for 4 hours. The reaction mixture was then cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The aqueous layer was acidified with 1N HCl and extracted with ethyl acetate three times. All the organic layers were combined, dried over magnesium sulfate, filtered, concentrated, and purified via silica gel chromatography (0-100% ethyl acetate in hexane) to afford the title compound.

후처리

  1. additionwas added
  2. temperaturethe solution was heated to 50° C. for 4 hours
  3. temperatureThe reaction mixture was then cooled to ambient temperature
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate three times
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via silica gel chromatography (0-100% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-9c0915778b7f4cab9abab802d34860c8
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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