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

HRID 222793

Reaction equation

HRID 222793 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-25eb500810574580a7fd558c165565ab
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Linked notes

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