Potassium Hydroxide → 4,4-Dimethyl-6-ethynyl-1,2,3,4-tetrahydroquinoline

HRID 2226559Notes

Reaction equation

HRID 2226559 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][Si](C)(C)C)[CH:10]=2)[NH:5][CH2:4][CH2:3]1.[OH-].[K+]>C(O)(C)C>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[CH:13])[CH:10]=2)[NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 156611344,4-Dimethyl-6-trimethylsilylethynyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 156611354,4-Dimethyl-6-ethynyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 569 mg (2.21 mmol) of 4,4-dimethyl-6-trimethylsilylethynyl-1,2,3,4-tetrahydroquinoline in 3 ml of isopropanol was added, under argon, 1 ml of 1N aqueous KOH solution. The reaction mixture was stirred at room temperature for 36 hours and the isopropanol was removed under vacuum. The residue was extracted with ether and the ether extract was washed successively with water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a brown oil.

Workup

  1. customthe isopropanol was removed under vacuum
  2. extractionThe residue was extracted with ether
  3. extractionthe ether extract
  4. washwas washed successively with water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0e1b11c1c5e44ab0ab1403f78aa6e7e6
Source dataset
uspto-grants-1994_09
Patent number
US05348972

Reaction notes

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