Ethyl Thioglycolate → 5-(Carbethoxymethylthio)-1-(2-furyl)-1-pentanol

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Reaction Steps

To a stirred, refluxing mixture of 76 g of ethyl mercaptoacetate, 79.5 g of 5-chloro-1-(2-furyl)-1-pentanol (Example 55), and 10 ml of 1.5 M sodium ethoxide in ethanol is added an additional 300 ml of 1.5 M sodium ethoxide during 15 minutes. The resulting mixture is stirred at reflux for 3 hours, cooled, and concentrated to remove most of the ethanol. The residue is partitioned with ether and water. The ether phase is washed with brine and dried over potassium carbonate. The solution is concentrated, diluted with xylene, and again concentrated to give an oil, pmr spectrum (CDCl3):δ3.24 (singlet, --S--CH2CO2C2H5) and 4.70 (triplet, CH2CHOH).

Provenance & Evidence