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

HRID 1467527ノート

反応式

HRID 1467527 の反応式
[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]

参加物

7

反応物 5

HCID 887MethanolHCID 7749Ethyl PropionateHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 10942334Sodium MethoxideHCID 178519069HCID 178519069、化合物

生成物 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-carboxylate収率 47%

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-b7bfb5e8a9ff4324840ac3d4aaf77422
出典データセット
uspto-grants-2015_04
特許番号
US08999987B2

反応ノート

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