Ethyl Propionate → HCID 67259334, compound

HRID 1968151Notes

Reaction equation

HRID 1968151 reaction equation
O=C1C2[C:5](=[C:6](/[N:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:23][CH2:22][CH2:21][N:20]4[C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])=[CH:15][CH:14]=3)C=CC=2)[CH2:4]O1.[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1.[CH3:43][CH2:44][O-:45].[Na+].[C:47]([O:51][CH2:52][CH3:53])(=[O:50])[CH2:48][CH3:49]>CCO>[CH2:27]([O:26][C:24]([N:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[C:16]1[CH:17]=[CH:18][C:13]([CH:12]2[CH:39]([C:38]3[CH:41]=[CH:42][C:35]([F:34])=[CH:36][CH:37]=3)[C:44](=[O:45])[C:43]3[C:48]([C:47]([O:51][CH2:52][CH3:53])=[O:50])=[CH:49][CH:4]=[CH:5][C:6]=3[NH:11]2)=[CH:14][CH:15]=1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 7749Ethyl PropionateHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxideHCID 178519068HCID 178519068, compound

Product 1

HCID 67259334HCID 67259334, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (E)-benzyl 2-(4-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)phenyl)pyrrolidine-1-carboxylate (0.5 g, 1.14 mmol) and 4-fluoro benzaldehyde (0.284 g, 2.28 mmol) in dry ethyl propionate (5 mL) was added EtONa (0.155 g, 2.28 mmol) in EtOH (6 mL), and the mixture was stirred at room temperature until the starting material was disappeared as monitored by TLC. Then the reaction mixture was quenched with 0.5 mL of water, the resulting mixture was concentrated in vacuo, and the residue was purified by column chromatography to give the title compound (130 mg, yield 20%) as a yellow solid. LC-MS (ESI) m/z: 592 (M+1)+.

Workup

  1. customThen the reaction mixture was quenched with 0.5 mL of water
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8545618c01aa47c6a4b48254f078121f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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