Potassium Hydroxide → (4,4-Dibutylthiochroman-6-yl)acetylene

Reaction equation

[OH-].[K+].[CH2:3]([C:7]1([CH2:23][CH2:24][CH2:25][CH3:26])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][Si](C)(C)C)[CH:15]=2)[S:10][CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6]>O.C(O)C>[CH2:3]([C:7]1([CH2:23][CH2:24][CH2:25][CH3:26])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[CH:18])[CH:15]=2)[S:10][CH2:9][CH2:8]1)[CH2:4][CH2:5][CH3:6]

Participants

Procedure

A solution of 1.41 g (25 mmol) of potassium hydroxide in 1.4 mL of water and 10.0 mL of ethanol was added to 1.44 g (4.00 mmol) of (4,4-dibutylthiochroman-6-yl)(trimethylsilyl)acetylene (Compound 34) and the resulting mixture stirred at room temperature for 16 hours during which time it became homogeneous. The solvent was removed in-vacuo and the residue was acidified with 5% aqueous H2SO4. The product was extracted with 2×50 mL of ether.