Ethyl chloroformate → HCID 21548938, compound

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Reaction Steps

2.54 g. of 2-(2-xanthenyl)-propionic acid is dissolved in 20 ml. of absolute THF and combined with 1 ml. of triethylamine. At -10°, a solution of 0.6 ml. of ethyl chloroformate in 4 ml. of THF is added dropwise within 15 minutes, the mixture is stirred for 30 minutes at -10° and then 0.5 g. of NaBH4 is introduced into the solution which contains the mixed anhydride of monoethyl carbonate and the aforementioned acid, 2-(2-xanthenyl)-4,6-dioxaoctane-3,5-dione. Thereafter, the mixture is stirred for 90 minutes at 25°, 10 ml. of water is added, the mixture extracted with ether, evaporated, and the thus-obtained residue refluxed for 30 minutes with a solution of 0.25 g. of KOH in 10 ml. of ethanol. After the ethanol has been distilled off, the mixture has been worked up as usual, and the product chromatographed on Al2O3, 2-(2-xanthenyl)-propanol is obtained, m.p. 86°-89°.

Provenance & Evidence