Water → Spiro[3.5]nonan-2-one

Participants

Reaction Steps

According to a literature procedure (Tetrahedron 1993, 49(36), 8159). A mixture of 1,1-dichlorospiro[3.5]nonan-2-one (5.00 g; 24.1 mmol) and zinc dust (4.74 g; 72.4 mmol) was stirred in acetic acid (60 mL) and water (30 mL) for 4 hours. The solution was then stored at −20° C. for 15 hours. The mixture was filtered through Celite®, washing with ether and hexane, and then the filtrate was washed with aqueous sodium hydroxide solution (2N; 4×100 mL). (This resulted in the precipitation of white salts, which needed to be removed by filtration). The organic phase was washed with water (30 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel, eluting with hexane/ether (10:1) to give the desired product as an almost colorless oil (2.56 g).

Provenance & Evidence