Potassium Hydroxide → 6-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinic acid

HRID 1707686Notes

Reaction equation

HRID 1707686 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][N:17]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[K+]>C(O)C.O>[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([OH:22])=[O:21])=[CH:18][N:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 15228883Ethyl 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinoate

Product 1

HCID 152288846-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]nicotinic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Absolute ethanol was degassed by applying a vacuum while simultaneously bubbling nitrogen through it. A solution of 188 mg (0.5201 mmol) ethyl 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronapth-2-yl)ethynyl]-nicotinoate in 2 ml absolute ethanol was treated with 800 ml of a 1.65M (1.32 mmol) solution of potassium hydroxide in ethanol and water. The mixture was stirred at room temperature for 18 hours and then the solvent removed in vacuo. The residue was dissolved in water and extracted with 50 ml ether, which was discarded. The aqueous layer was then acidified with glacial acetic acid and extracted with 4×50 ml ether. The ether extracts were combined, washed with water, saturated NaCl solution and then dried (MgSO4). Solvent was removed in vacuo to give the title compound as a pale yellow solid. PMR (CDCl3): δ 1.31 (12H, s), 1.71(4H, s), 7.34 (1H, d, J~7.8 Hz), 7.40 (1H, d, J~7.8 Hz), 7.62 (1H, s), 8.39 (1H, dd, J~7.3 Hz, 2.1 Hz), 9.33 (1H, d, J~2.1 Hz).

Workup

  1. customAbsolute ethanol was degassed
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with 50 ml ether, which
  5. extractionextracted with 4×50 ml ether
  6. washwashed with water, saturated NaCl solution
  7. dry with materialdried (MgSO4)
  8. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-e6180e5a68244a448b6f89b44d140d97
Source dataset
uspto-grants-1994_10
Patent number
US05354776

Reaction notes

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