Methanol → 1-Cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

HRID 1935836Notes

Reaction equation

HRID 1935836 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([C:14]#[C:15][Si](C)(C)C)=[CH:11][CH:12]=3)[C:7]([CH3:21])([CH3:20])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.CO.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CCCCCC>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([C:14]#[CH:15])=[CH:11][CH:12]=3)[C:7]([CH3:21])([CH3:20])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 225687951-Cyclopropyl-6-trimethylsilanylethynyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline2×

Product 1

HCID 225688711-Cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following general procedure E and using 1-cyclopropyl-6-trimethylsilanylethynyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (Intermediate 52, 0.40 g, 1.34 mmol), methanol and potassium carbonate (0.2 g, 1.47 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 2% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.17 g, 56%).

Sources & evidence

ORD record
ord-bafbf41afdc248dc8e5e77127c247c5f
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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