Potassium Carbonate → HCID 18931443, compound

HRID 1598965Notes

Reaction equation

HRID 1598965 reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18931458HCID 18931458, compound2×

Product 1

HCID 18931443HCID 18931443, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.050 g (0.15 mmol) of 4,4-dimethyl-1,2,3,4-tetrahydro-N-phenyl-7-[2-(trimethylsilyl)ethynyl]quinoline (Compound 7) in 4.0 mL of methanol was added 0.032 g (0.23 mmol) of potassium carbonate, and the resulting mixture was stirred at room temperature for 20 hours. The mixture was then concentrated in vacuo, water was added, and the mixture was extracted with diethyl ether (2x). The organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound as an oil. PNMR (300 MHz, CDCl3) d 1.34 (6 H, s), 1.84 (2 H, t, J=6.0 Hz), 2.88 (1 H, s), 3.62 (2 H, t, J=6.0 Hz), 6.82 (1 H, d, J=1.6 Hz), 6.85 (1 H, rid, J=7.9, 1.6 Hz), 7.13-7.39 (6 H, m).

Workup

  1. concentrationThe mixture was then concentrated in vacuo, water
  2. additionwas added
  3. extractionthe mixture was extracted with diethyl ether (2x)
  4. washThe organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6d43850b6b84dd39a55b5f2c0159d0a
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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