Potassium Carbonate → 6-Ethynyl-2,2-dimethylchroman-4-one

HRID 619648Notes

Reaction equation

HRID 619648 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]#[C:14][Si](C)(C)C)[CH:8]=2)[O:3]1.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[CH3:1][C:2]1([CH3:19])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]#[CH:14])[CH:8]=2)[O:3]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 218466592,2-Dimethyl-6-trimethylsilanylethynyl-chroman-4-one2×

Product 1

HCID 218466816-Ethynyl-2,2-dimethylchroman-4-oneYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,2-dimethyl-6-trimethylsilanylethynyl-chroman-4-one (Compound 261, 4.05 g, 14.87 mmol) in 60.0 mL of MeOH was added K2CO3 (410.9 mg, 2.97 mmol) The resulting mixture was stirred at room temperature for 24 hours, diluted with EtOAc (100 mL) and washed with H2O and saturated aqueous NaCl, and dried over Na2SO4. Concentration of this solution under reduced pressure afforded 2.71 g (91%) of the product as a tan solid. 1H NMR (300 MHz, CDCl3) δ: 8.01 (1H, d, J=2.2 Hz), 7.56 (1H, dd, J=2.2, 8.6 Hz), 6.90 (1H, d, J=8.6 Hz), 3.02 (1H, s), 2.74 (2H, s), 1.47 (6H, s).

Workup

  1. washwashed with H2O and saturated aqueous NaCl
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-2907a7adb8414ae3938bbffaabc33c4f
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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