Potassium Carbonate → HCID 21957876, compound

HRID 918795Notes

Reaction equation

HRID 918795 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-trimethylsilanylethynylthiochroman-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-440eb576dccc4716a6192a3c366f500c
Source dataset
uspto-grants-2016_03
Patent number
US09271946B2

Reaction notes

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