4-Methylthiazole → 2-Acetyl-4-methylthiazole

HRID 1178198노트

반응식

HRID 1178198 반응식
[Li]CCCC.[CH3:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1.CON(C)[C:15](=[O:17])[CH3:16]>CCOCC>[CH3:6][C:7]1[N:8]=[C:9]([C:15](=[O:17])[CH3:16])[S:10][CH:11]=1

참가 물질

5

반응물 3

HCID 127484-MethylthiazoleHCID 537505N-Methoxy-N-methylacetamideHCID 178418339Butyllithium

생성물 1

HCID 53247972-Acetyl-4-methylthiazole수율 85%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a stirred solution of n-BuLi (2M in pentane; 22.4 mL, 0.045 mol) in 70 mL of dry ether at −78° C. was added dropwise 4-methylthiazole (3.7 g, 0.037 mol) in 30 mL of ether over a period of 30 minutes. The mixture was stirred for 1 h, then N-methoxy-N-methylacetamide (4.37 mL, 0.041 mol) was added dropwise over 10 minutes. After 1 h of stirring at −78° C. the reaction mixture was washed with sat'd NaHCO3 and extracted with ether. The organic layer was dried with Na2SO4 and concentrated in vacuo to give 4.38 g (85%) of 2a as an oil that was used directly for the next step. 1H NMR (CDCl3) δ 7.2 (s, 1H), 2.75 (s, 3H), 2.5 (s, 3H).

후처리

  1. stirringAfter 1 h of stirring at −78° C. the reaction mixture
  2. washwas washed with sat'd NaHCO3
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fbe8899a89ce4e0381341edcbacf41d6
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276502B2

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