Potassium Carbonate → HCID 21957876, compound

HRID 2213553Notes

Reaction equation

HRID 2213553 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, compound

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 (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 6-ethynyl-2,2-dimethylthiochroman-4-one 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-73cc34ff8f8c4b6c801e3e864f35d1a3
Source dataset
uspto-grants-2006_09
Patent number
US07105566B2

Reaction notes

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