Reaction #1005977

Reaction equation

2,2-dimethyl-6-trimethylsilanylethynylthiochroman-4-one

K2CO3

→

6-ethynyl-2,2-dimethylthiochroman-4-one

Yield 99.0%

Solvents

H2O

MeOH

Conditions

Workup

1. 1
   Extractionextracted with Et2O
2. 2
   WashThe combined organic layers were washed with H2O and saturated aqueous NaCl
3. 3
   Dryingdried over MgSO4
4. 4
   OtherRemoval of the solvent under reduced pressure

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).

Source