Ethyl Propionate → Ethyl 2-(4-(diethoxymethyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968010Notes

Reaction equation

HRID 1968010 reaction equation
[CH2:1]([O:3][CH:4]([O:23][CH2:24][CH3:25])[C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:20])=[CH:7][CH:6]=1)[CH3:2].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.[O-][CH2:36][CH3:37].[Na+].C(OCC)(=[O:42])CC>>[CH2:1]([O:3][CH:4]([O:23][CH2:24][CH3:25])[C:5]1[CH:22]=[CH:21][C:8]([CH:9]2[CH:31]([C:30]3[CH:33]=[CH:34][C:27]([F:26])=[CH:28][CH:29]=3)[C:13](=[O:42])[C:12]3[C:16]([C:15]([O:14][CH2:36][CH3:37])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 4

HCID 7749Ethyl PropionateHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxideHCID 178470922HCID 178470922, compound

Product 1

HCID 67258671Ethyl 2-(4-(diethoxymethyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 26%

Procedure

A solution of (E)-4-(4-(diethoxymethyl)benzylideneamino)isobenzofuran-1(3H)-one (10.8 g, 31.9 mmol) and 4-fluorobenzaldehyde (3.95 g, 31.9 mmol) in ethyl propionate (150 mL) was added sodium ethoxide (8.66 g, 127.4 mmol, in ethanol 60 ml) at 0° C. Then the mixture was stirred at room temperature for 5 hr. The resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 1:1) to give the crude product (4.2 g, yield 26%). LC-MS (ESI) m/z: 492 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 1:1)

Sources & evidence

ORD record
ord-4e8f3710e89b40a280a0af29ad05ed0b
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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