Potassium Carbonate → 6-Ethynylthiochroman-4-one

HRID 1417687Notes

Reaction equation

HRID 1417687 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]2[S:13][CH2:12][CH2:11][C:10](=[O:14])[C:9]=2[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:4]([C:5]1[CH:6]=[CH:7][C:8]2[S:13][CH2:12][CH2:11][C:10](=[O:14])[C:9]=2[CH:15]=1)#[CH:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 154909942,3-dihydro-6-(2-trimethylsilylethynyl)-(4H)-1-benzothiopyran-4-one

Product 1

HCID 223237716-Ethynylthiochroman-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution containing 600.0 mg (2.25 mmol) of 2,3-dihydro-6-(2-trimethylsilylethynyl)-(4H)-1-benzothiopyran-4-one and 100.0 mg (0.72 mmol) K2CO3 in 15 ml MeOH was stirred at room temperature for 20 hours. The solution was diluted with H2O and extracted with Et2O. The combined organic layers were washed with H2O and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents under reduced pressure afforded the title compound as an orange solid. 1H NMR (CDCl3): δ 8.17 (1H, d, J=1.8 Hz), 7.40 (1H, dd, J=1.8, 8.2 Hz), 7.19 (1H, d, J=8.2 Hz), 3.22 (2H, t, J=6.3 Hz), 3.08 (1H, s) 2.94 (2H, t, J=6.3 Hz).

Workup

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

Sources & evidence

ORD record
ord-0998a91b4b4b49b19d80b54469790eff
Source dataset
uspto-grants-1999_03
Patent number
US05877207

Reaction notes

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