Ethanethiol → HCID 13882884, compound

Participants

Reaction Conditions

Reaction Steps

Ethanethiol (5.33 ml, 0.072 mol) followed by 14.72 g (0.046 mol) of product of Example 19 was added to a solution of sodium ethoxide prepared from 1.66 g (0.072 mol) of sodium in 100 ml of ethanol and stirred at reflux overnight. The reaction mixture was filtered, poured into 200 ml of water, extracted with ether, washed with 10% NaOH, dried (MgSO4) and concentrated in vacuo to 9.45 g of yellow oil. This oil in 150 ml of CH2Cl2 was cooled to 5° C. and 3.73 g (0.022 mol) of MCPBA was added. Reaction was monitored by TLC. The reaction mixture was filtered, washed with NaHCO3, dried (MgSO4) and concentrated in vacuo to give 5.06 g of yellow oil. This was purified by HPLC using 10% ethyl acetate/cyclohexane as eluting solvent to give 3.81 g (65.6%) of an oil. A portion (1.71 g) of this oil was kugelhohr distilled at 22 Pa, pot temperature 95° C., affording 1.45 g of product as a clear oil, nD25 1.4575.

Provenance & Evidence