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1,1'-Carbonyldiimidazole → Ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate

HRID 1274860
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HRID 1274860 반응식
C([Mg]Br)(C)C.[C:6]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:7][C:8]([O-:10])=O.[CH3:15][C:16]1[O:21][CH2:20][N:19]([C:22](C)([CH3:26])[C:23](O)=O)[C:18](=[O:28])[C:17]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N-]1C=CN=C1>O1CCCC1.CCOCC>[CH3:15][C:16]1[O:21][CH2:20][N:19]([C:22]([CH3:26])([CH3:23])[C:8](=[O:10])[CH2:7][C:6]([O:12][CH2:13][CH3:14])=[O:11])[C:18](=[O:28])[C:17]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
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참가 물질

8

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HCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 3595298Propanedioic acid, monoethyl esterHCID 221182822-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionic acidHCID 178418365HCID 178418365, 화합물

생성물 1

HCID 22118254
Ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate
수율 55.8%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

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온도
40 °C

실험 절차

Isopropyl magnesium bromide (0.7M solution in tetrahydrofuran) was added to a solution of monoethyl malonate(1.44 g) in tetrahydrofuran at 0° C. The mixture was stirred at 20° C. for 0.5 hour and at 40° C. for 0.5 hour. 2-(2,3-Dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)2-methylpropionic acid (2 g) and carbonyldiimidazole (1.42 g) was stirred in tetrahydrofuran for 8 hours and the resulting imidazolide solution then added to the above mixture at 0° C., stirred at 20° C. for 3 hours and refluxed for 2 hours. The mixture was diluted (ether), washed (5% hydrochloric acid), dried (MgSO4),evaporated and the residue purified by column chromatography (ethyl acetate/hexane 1:2) to give ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate (Compound 200, 1.4 g), NMR 1.25(3H, t), 1.47(6H, s), 1.94(3H, s), 3.60(2H, s), 4.15(2H, q), 5.26(2H, s), 7.2-7.4(5H, m).

후처리

  1. stirringstirred at 20° C. for 3 hours
  2. temperaturerefluxed for 2 hours
  3. washwashed (5% hydrochloric acid), dried (MgSO4),evaporated
  4. customthe residue purified by column chromatography (ethyl acetate/hexane 1:2)

출처 및 근거

ORD 기록
ord-810835ea14d34b80864c11098e0b7f0c
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06159902

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