Hydrochloric Acid → HCID 18980428, compound

Participants

Reaction Steps

23.7 g (150 mmole) 1,4-dioxa-spiro[4.5]decan-8-ol were dissolved in 120 ml dimethylformamide and stirred for 1 hour in a nitrogen atmosphere at room temperature with 7.2 g (159 mmole) of 50% sodium hydride in mineral oil. 38 g (150 mmole) toluene-4-sulphonic acid cyclopentylmethyl ester were then added (Krapcho, Johnson, J. Org. Chem., 36, 146, (1971). The mixture was stirred at room temperature and cooled to a temperature between 5° C. and 10° C. 125 ml water were then added dropwise. The product was extracted with ether and dried over sodium sulphate, and the solvent was removed by distillation. The product obtained (32 g) was dissolved in diisopropyl ether and stirred for 20 hours with 65 ml water and 95 ml concentrated hydrochloric acid. It was then neutralised with sodium hydrogen carbonate, extracted with ether and dried over sodium sulphate. The oil obtained (23.4 g) was purified with 1:1 diisopropyl ether/n-hexane via a silica gel column. 17.5 g of compound (61) were obtained (60% theoretical).

Provenance & Evidence