Potassium Carbonate → 4,4-Dimethyl-2-iso-propoxy-3,4-dihydro-7-ethynylquinoline

HRID 52448Notes

Reaction equation

HRID 52448 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[NH:5][CH:4]([O:18][CH:19]([CH3:21])[CH3:20])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([O:18][CH:19]([CH3:20])[CH3:21])[CH2:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 199637264,4-Dimethyl-2-iso-propoxy-1,2,3,4-tetrahydro-7-[(trimethylsilyl)ethynyl]quinoline2×

Product 1

HCID 199637244,4-Dimethyl-2-iso-propoxy-3,4-dihydro-7-ethynylquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.14 g (0.45 mmol) of 4,4-dimethyl-2-iso-propoxy-1,2,3,4-tetrahydro-7-[(trimethylsilyl)ethynyl]quinoline (Compound 26) in 2.5 ml of methanol was added 0.10 g (0.72 mmol) of potassium carbonate. The reaction mixture was then stirred at room temperature for 2.5 h. The reaction mixture was then concentrated in vacuo and the resulting oil was dissolved in water and extracted with methylene chloride (2×). The organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an oil. This compound was used for the next reaction without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe resulting oil was dissolved in water
  3. extractionextracted with methylene chloride (2×)
  4. dry with materialThe organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b49daf3eaa64ffa90521ef7140c9676
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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