Acetic Anhydride → (6-Cyano-3-methyl-2-pyridinyl)methyl acetate

HRID 2356626노트

반응식

HRID 2356626 반응식
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][C:9]1C(C)=[N+:13]([O-])[C:12]([C:17]#[N:18])=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>>[C:5]([O:4][CH2:1][C:2]1[C:9]([CH3:8])=[CH:10][CH:11]=[C:12]([C:17]#[N:18])[N:13]=1)(=[O:7])[CH3:6]

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 68455695HCID 68455695, 화합물

생성물 1

HCID 68457478(6-Cyano-3-methyl-2-pyridinyl)methyl acetate수율 67%

반응 조건

온도
120 °C

실험 절차

To acetic anhydride (12 ml) at 120° C. was added 5,6-dimethyl-2-pyridine-carbonitrile 1-oxide (3.02 g) and the solution heated at 120° C. for 5 minutes then under reflux for 2.5 hours. After cooling the solution was added to ice (ca. 80 g) and the mixture neutralized with sodium bicarbonate. It was extracted with ether (80 ml then 2×40 ml) and the combined extracts washed with brine (40 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by Biotage chromatography eluting with 2:1 hexane:ethyl acetate to afford the title compound (2.60 g, 67%) as a pale yellow solid. LC/MS [MH+]=191, RT=2.05 min.

후처리

  1. temperatureunder reflux for 2.5 hours
  2. temperatureAfter cooling the solution
  3. extractionIt was extracted with ether (80 ml
  4. wash2×40 ml) and the combined extracts washed with brine (40 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Biotage chromatography
  8. washeluting with 2:1 hexane

출처 및 근거

ORD 기록
ord-e3f3ca37c7db45c4af1c05e45434686f
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759369B2

반응 노트

불러오는 중…