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

HRID 344956Notes

Reaction equation

HRID 344956 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 in vacuo and the residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title as a brown oil. PMR (CDCl3): & 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 in vacuo
  7. customthe residue was purified by flash chromatography (silica; 10% ethyl acetate in hexanes)
  8. customto give the title as a brown oil

Sources & evidence

ORD record
ord-79720b1a071c4e96808038c78036f4ce
Source dataset
uspto-grants-1991_10
Patent number
US05053523

Reaction notes

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