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Water → HCID 19756351, 화합물

HRID 1587826
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HRID 1587826 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6][CH:7]=1.[C:29]([CH2:33][C:34](OC)=[O:35])(=O)[CH2:30][CH3:31].O>C1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Si:12]([O:11][CH2:10][CH2:9][O:8][C:5]1[N:6]=[C:7]2[C:2](=[CH:3][CH:4]=1)[NH:1][C:29]([CH2:30][CH3:31])=[CH:33][C:34]2=[O:35])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
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참가 물질

6

반응물 3

HCID 962WaterHCID 121699Methyl 3-oxovalerateHCID 19756412HCID 19756412, 화합물

생성물 1

HCID 19756351HCID 19756351, 화합물수율 51.4%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 8078Cyclohexane용매

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온도
260 °C

실험 절차

A solution of compound C (89.5 g), methyl propionylacetate (32.8 g) and p-toluenesulphonic acid (1.0 g) in cyclohexane (900 ml) was heated under reflux with azeotropic removal of water for 20 hours. Volatile material was then removed from the reaction mixture by evaporation and the residue was dissolved in ethyl acetate (1 l). The solution was washed with saturated sodium hydrogen carbonate solution (500 ml), water (500 ml), saturated sodium chloride solution (500 ml), and then dried (MgSO4). The solvent was removed by evaporation and the residue dissolved in a eutectic mixture of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (750 ml). The solution was heated to 260° C. and the temperature maintained for 30 minutes. The solution was cooled and diluted with hexane (1 l) to give 6-[2-(t-butyldiphenylsilyl)oxyethoxy]-2-ethyl-1,5-naphthyridin-4(1H)-one (D) (55.4 g), as a white solid, m.p. 209°-210° C.; NMR (d6 -DMSO): 1.1(s,9H), 1.35(t,3H), 2.8(q,2H), 4.15(t,2H), 4.65(t,2H), 6.3(br s,1H), 7.25(d,1H), 7.5-7.6(m,7H), 7.65-7.8(m,4H), 8.1(d,1H).

후처리

  1. customVolatile material was then removed from the reaction mixture by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate (1 l)
  3. washThe solution was washed with saturated sodium hydrogen carbonate solution (500 ml), water (500 ml), saturated sodium chloride solution (500 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. dissolutionthe residue dissolved in a eutectic mixture of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (750 ml)
  7. temperaturethe temperature maintained for 30 minutes
  8. temperatureThe solution was cooled
  9. additiondiluted with hexane (1 l)

출처 및 근거

ORD 기록
ord-c6a335c15aa345fbbb468bf74837cc62
출처 데이터셋
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05219863

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