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

HRID 6557Notes

Reaction equation

HRID 6557 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-tetrahydroquinoline2×

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 (Compound 95) 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 h 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 vacuo and the residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a brown oil. PMR (CDCl3): δ 1.26 (6H, s), 1.65-1.72 (2H, m), 2.96 (1H, s), 3.27-3.34 (2H, m), 6.34 (1H, d, J~8.3 Hz), 7.08 (1H, dd, J~8.3 Hz, 1.6 Hz), 7.33 (1H, d, J~1.6 Hz).

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 vacuo
  7. customthe residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-413684e85ed6442a83d777131c638b39
Source dataset
uspto-grants-1993_09
Patent number
US05248777

Reaction notes

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