Potassium Carbonate → HCID 21957876, compound

HRID 619621Notes

Reaction equation

HRID 619621 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)[S:3]1.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:13]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[S:3][C:2]([CH3:1])([CH3:19])[CH2:11][C:10]2=[O:12])#[CH:14]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21957873HCID 21957873, compound2×

Product 1

HCID 21957876HCID 21957876, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2,2-dimethyl-6-trimethylsilanylethynyl-thiochroman-4-one (Compound 221, 110.0 mg, 0.38 mmol) and K2CO3 (40.0 mg, 0.29 mmol) in 10.0 mL MeOH was stirred overnight at room temperature. The solution was diluted with H2O and extracted with Et2O. The combined organic layers were washed with H2O and saturated aqueous NaCl and dried over MgSO4. Removal of the solvent under reduced pressure afforded 81 mg (99%) of the title compound as an orange oil. 1H NMR (300 MHz, CDCl3) δ:8.20 (1H, d, J=1.9 Hz), 7.46 (1H, dd, J=1.9, 8.1 Hz), 7.18 (1H, d, J=8.1 Hz), 3.08 (1H, s), 2.86 (2H, s), 1.46 (6H, s).

Workup

  1. extractionextracted with Et2O
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b9dca658be824ae088d4d7b87ccb0dd6
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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