Diethyl Oxalate → 4-[1-(4-fluorobenzyl)-5-phenyl-1H-pyrrol-2-yl]-2,4-dioxobutyric acid ethyl ester

HRID 381502Notes

Reaction equation

HRID 381502 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]=[C:8]2[C:18](=[O:20])[CH3:19])=[CH:4][CH:3]=1.C1COCC1.[C:28](OCC)(=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].CC[O-].[Na+]>CCOC(C)=O>[CH2:32]([O:31][C:29](=[O:30])[C:28](=[O:34])[CH2:19][C:18]([C:8]1[N:7]([CH2:6][C:5]2[CH:21]=[CH:22][C:2]([F:1])=[CH:3][CH:4]=2)[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:9]=1)=[O:20])[CH3:33]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 8028TetrahydrofuranHCID 2723922Sodium ethoxideHCID 183634681-[1-(4-fluorobenzyl)-5-phenyl-1H-pyrrol-2-yl]ethanone

Product 1

HCID 206968514-[1-(4-fluorobenzyl)-5-phenyl-1H-pyrrol-2-yl]-2,4-dioxobutyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round bottomed flask with a stirring bar and an argon inlet was added 1-[1-(4-fluorobenzyl)-5-phenyl-1H-pyrrol-2-yl]ethanone AV-8-1 (0.628 g, 2.14 mmol), dry THF (10 mL), diethyl oxalate (0.41 mL, 3.00 mmol) and NaOEt (0.204 g, 3.00 mmol). The resulting mixture was stirred 1 h at ambient temperature. The mixture was diluted with EtOAc and washed with 1N HCl, H2O (2×) and brine. Drying (MgSO4) filtration and removal of the solvent in vacuo gave 4-[1-(4-fluorobenzyl)-5-phenyl-1H-pyrrol-2-yl]-2,4-dioxobutyric acid ethyl ester AV-9-1 as an oil. This material was used without further purification. 1H NMR (CDCl3) δ 1.38 (3H, t, j=7.1 Hz), 4.38 (2H, q, j=7.1 Hz), 5.65 (2H, s), 6.38 (1H, d, j=4.1 Hz), 6.79 to 6.94 (4H, m), 7.29 (2H, m), 7.39 (3H, m).

Workup

  1. washwashed with 1N HCl, H2O (2×) and brine
  2. customDrying
  3. filtration(MgSO4) filtration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-d230e3e968d04d47a9397c01db2a7953
Source dataset
uspto-grants-2001_10
Patent number
US06306891B1

Reaction notes

Loading…