Réaction #6633

Équation de réaction

trimethylsilyl (4,4,7-trimethyl-thiochroman-6-yl) ethyne

Compound 67

4,4,7-Trimethyl-6-trimethylsilylethynyl-thiochroman

potassium hydroxide

→

title compound

4,4,7-Trimethyl-6-ethynyl-Thiochroman

Solvants

isopropanol

Conditions de réaction

Traitement

1. 1
   Autrewas degassed under nitrogen
2. 2
   ConcentrationThe mixture was concentrated under vacuum
3. 3
   Extractionextracted with 2×10 ml of ether
4. 4
   Lavagewashed successively with water and saturated NaCl solution
5. 5
   Séchagedried (MgSO4)
6. 6
   AutreThe solvent was removed in vacuo

Mode opératoire

A mixture of 380 mg (1.69 mmol of trimethylsilyl (4,4,7-trimethyl-thiochroman-6-yl) ethyne, (Compound 67) 4 ml of isopropanol and 2.5 ml of aqueous 1N potassium hydroxide was degassed under nitrogen and stirred at room temperature for 16 h. The mixture was concentrated under vacuum and extracted with 2×10 ml of ether. The ether extracts were combined and washed successively with water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo to give the title compound as a yellow oil. PMR (CDCl3): δ 1.31 (6H, s), 1.88-1.96 (2H, m), 2.35 (3H, s), 3.00-3.08 (2H, m), 3.25 (1H, s), 6.94 (1H, s), 7.47 (1H, s).

Source