Toluene → Ethyl 1-(4-chlorophenylsulfonyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate

HRID 15740

Reaction equation

HRID 15740 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]=[C:19]=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C[O:22]C=CC([Si](C)(C)C)=C.[C:31]1([CH3:37])C=CC=C[CH:32]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([N:18]2[CH:19]=[CH:37][C:31](=[O:22])[CH2:32][CH:2]2[C:1]([O:5][CH2:6][CH3:7])=[O:4])(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 1385874-Chlorobenzenesulfonyl isocyanateHCID 866134601-Methoxy-3-trimethylsilyl-1,3-butadiene

Product 1

HCID 59342383Ethyl 1-(4-chlorophenylsulfonyl)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylateYield 34%

Procedure

A solution of ethyl glyoxalate (27 mL, 0.14 mol) and 4-chlorobenzene sulfonylisocyanate (20 mL, 0.14 mol) in toluene (300 mL) was heated at reflux for 60 hours. The reaction mixture was cooled to room temperature and 1-methoxy-3-trimethylsilyl-1,3-butadiene (27 mL, 0.14 mol) was added, The reaction was heated at 50° C. for 18 hours. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (20% EtOAc/hexanes) to yield 16.0 g (34%) of compound 103 as a yellow oil. 1H NMR (CDCl3) δ 7.81 (d, 2H), 7.67 (dd, 1H), 7.55 (d, 2H), 5.40 (d, 1H), 5.01-4.97 (m, 1H), 4.13-4.03 (m, 3H), 2.86-2.81 (m, 2H), 1.16 (t, 3H).

Workup

  1. temperatureat reflux for 60 hours
  2. temperatureThe reaction was heated at 50° C. for 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b368fd23c59347eab5cf35ba6b8dfa43
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Linked notes

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