Tetrahydrofuran → 4-Ethyl-2-methyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

HRID 222793

反応式

HRID 222793 の反応式
[NH:1]([C:8]([CH3:15])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[C:21](OCC)(=[O:26])[C:22]#[C:23][CH2:24][CH3:25]>>[CH2:13]([O:12][C:10]([C:9]1[C:23]([CH2:24][CH3:25])=[CH:22][C:21](=[O:26])[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]=1[CH3:15])=[O:11])[CH3:14]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 94928Ethyl 3-anilinobut-2-enoateHCID 99169Ethyl pent-2-yn-1-oate

生成物 1

HCID 583074524-Ethyl-2-methyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

実験手順

To a stirred solution of ethyl 3-anilinobut-2-enoate (50 mg, 0.2 mmol) in tetrahydrofuran (1 mL, 10 mmol) sodium hydride (60% NaH in mineral oil, 9.7 mg) was added. After 15 min ethyl 2-pentynoate (0.039 mL, 0.292 mmol) was added. After 60 min it was partitioned between ether (9 mL) and sat. aq. NaHCO3 (3 mL). The organic phase was washed twice with sat. aq. NaHCO3, dried (MgSO4) and evaporated. LC-MS (m/z) 286.3 (MH+); tR=1.27 (method C). 1H NMR (500 MHz, DMSO-d6): 1.13 (t, J=7.4 Hz, 3H, Me of Et), 1.28 (t, J=7.1 Hz, 3H, Me of EtO), 1.89 (s, 3H, 2-Me), 2.49 (q (overlapping with DMSO), J=7.4 Hz, 2H, CH2 of Et), 4.28 (q, J=7.1 Hz, 2H, CH2 of EtO), 6.28 (s, 1H, C5-H), 7.27 (t, J=7.3 Hz, 2H, two ortho-H of Ph), 7.47 (t, J=7.3 Hz, 1H, para-H of Ph), 7.53 (t, J=7.5 Hz, 2H, two meta-H of Ph).

後処理

  1. customAfter 60 min it was partitioned between ether (9 mL) and sat. aq. NaHCO3 (3 mL)
  2. washThe organic phase was washed twice with sat. aq. NaHCO3
  3. dry with materialdried (MgSO4)
  4. customevaporated

出典と根拠

ORDレコード
ord-25eb500810574580a7fd558c165565ab
出典データセット
uspto-grants-2012_06
特許番号
US08207347B2

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