Methanol → Ethyl 3-(4-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1967907노트

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HRID 1967907 반응식
[CH:1](=[N:8]/[C:9]1[CH:17]=[CH:16]C=[C:14]2[C:10]=1[CH2:11][O:12][C:13]2=O)\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:21][CH:22]([O:31][CH2:32][CH3:33])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)[CH3:20].[CH3:34][O-:35].[Na+].CO.[C:39]([O:43][CH2:44][CH3:45])(=[O:42])[CH2:40][CH3:41]>>[CH2:19]([O:21][CH:22]([O:31][CH2:32][CH3:33])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]2[C:34](=[O:35])[C:41]3[C:40]([C:39]([O:43][CH3:44])=[O:42])=[CH:13][CH:14]=[CH:10][C:9]=3[NH:8][CH:1]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:25][CH:24]=1)[CH3:20].[CH2:19]([O:21][CH:22]([O:31][CH2:32][CH3:33])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]2[C:11](=[O:12])[C:10]3[C:40]([C:39]([O:43][CH2:44][CH3:45])=[O:42])=[CH:41][CH:16]=[CH:17][C:9]=3[NH:8][CH:1]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:25][CH:24]=1)[CH3:20]

참가 물질

7

반응물 5

HCID 887MethanolHCID 7749Ethyl PropionateHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 10942334Sodium MethoxideHCID 178519069HCID 178519069, 화합물

생성물 2

HCID 67259144Methyl 3-(4-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateHCID 67260501Ethyl 3-(4-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate수율 47%

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온도
0 °C

실험 절차

A mixture of (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (474 mg, 2 mmol) and 4-(diethoxymethyl)benzaldehyde (0.40 g, 2.4 mmol) in ethyl propionate (15 mL) was cooled to 0° C. A solution of sodium methoxide in methanol [sodium (184 mg, 8 mmol) in methanol (15 mL)] was then added dropwise. After the addition, the mixture was stirred at 25° C. for 18 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=100:1 to 10:1) to give methyl 3-(4-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 3-(4-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (430 mg, yield: 47%) as a light yellow solid. LC-MS (ESI) m/z: 460 (M+1)+ and 474 (M+1)+.

후처리

  1. additionAfter the addition
  2. customThe mixture was quenched with water (10 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (50 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give crude product
  10. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=100:1 to 10:1)

출처 및 근거

ORD 기록
ord-8b2f01f9875542098f926717fe2c05ba
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420650B2

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