Tetrahydrofuran → 2,2-Diethyl-1,2-dihydroquinoline

HRID 850354Notes

Reaction equation

HRID 850354 reaction equation
C[C:2]1([CH3:12])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.CCO[C:16]([CH3:18])=O.[CH2:19]1COCC1>Cl[Cu]>[CH2:12]([C:2]1([CH2:16][CH3:18])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1)[CH3:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 124373012,2-Dimethyl-1,2-dihydroquinoline

Product 1

HCID 104878352,2-Diethyl-1,2-dihydroquinolineYield 50%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

This compound was prepared in a manner similar to that described for 1,2-Dihydro-2,2-dimethylquinoline (structure 17 of Scheme III, where R1 =R2 =Me) from 2-ethyl-1-pentyn-3-yl(phenyl)amine (3.00 g, 16.0 mmol) and CuCl (0.190 g, 1.92 mmol) in THF to afford 1.51 g (50%) of 2,2-diethyl-1,2-dihydroquinoline after flash chromatography (hexanes:EtOAc, 16:1). Data for 2,2-diethyl-1,2-dihydroquinoline: Rf 0.44 (16:1 hexanes:EtOAc; 1H NMR (400 MHz, CDCl3) 6.85-6.95 (m, 1H), 6.81 (d, J=7.3, 1H), 6.48 (t, J=7.3, 1H), 6.36 (d, J=9.9, 1H), 5.21 (d, J=9.9, 1H), 3.39 (broad s, 1H), 1.35-1.55 (m, 4H), 0.93 (t, J=7.5, 6H).

Workup

  1. customThis compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-cbb85298317e4a12a0bee988a3d8ddd4
Source dataset
uspto-grants-2000_01
Patent number
US06017924

Reaction notes

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