Triethylamine → HCID 86742995, compound

Participants

Reaction Steps

A solution of 3.5 g (0.0148 mol) of (6E,10Z)-12-hydroxy-2,6,10-trimethyl-1,6,10-dodecatrien-3-one in 110 ml of methanol is treated with 7.15 g of N-(2-acetylthioethyl)acetamide and 6.2 ml of triethylamine. The solution is stirred under argon at room temperature for 24 hours. The solvents are removed on a rotary evaporator. The residue is taken up three times with toluene and freed from solvent on a rotary evaporator. The crude product can be used directly for the acetylation described in Example 12 or can be chromatographed on silica gel with ether-methanol 15:1. After chromatographic purification there is obtained (2Z,6E)-12-[(2-acetamidoethyl)thio]-3,7,11-trimethyl-10-oxo-2,6-dodecadien-1-ol which exhibits the following bands in the IR spectrum: 1737 cm-1, 1715 cm-1, 1437 cm-1, 1366 cm-1, 1277 cm-1,1235 cm-1, 1157 cm-1, 1136 cm-1, 1022 cm-1.

Provenance & Evidence