2-BroMo-5,8-dioxaspiro[3.4]octane synthesis

Yield:-

Reaction Conditions:

with pyridinium p-toluenesulfonate in benzene for 12 h;Reflux;

Steps:

100
A mixture of 3-bromocyclobutanone (Compound 100F, 5.9 g, 39.6 mmol), 1 ,2-ethanediol (8.6 mL, 158.4 mmol) and PPTS (1.9 g, 7.92 mmol) in benzene (40 mL) was heated to reflux in a Dean-Stark apparatus. After 12 h, the reaction mixture was allowed to cool and washed with water (2 x 30 ml_). The organic phase was dried (Na₂SO₄) and concentrated and the residue was purified by column chromatography (ethyl acetate/ hexanes: 1 :5) to give 984 mg of 2- bromo-5,8-dioxa-spiro[3.4]octane. ¹H NMR (CDCI₃, 300 MHz): δ = 2.77-2.82 (m, 2 H), 2.95- 3.00 (m, 2 H), 4.19-4.23 (m, 1 H).

References:

OSI PHARMACEUTICALS, INC.;APPARI, Rama, Devi;CHEN, Xin;CHILUKURI, Ramesh;CREW, Andrew, P.;DONG, Hanqing;FERRARO, Caterina;FOREMAN, Kenneth;GUPTA, Ramesh, C.;LI, An-hu;SHERMAN, Dan;STOLZ, Kathryn, M.;VOLK, Brian;ZAHLER, Robert WO2010/141406, 2010, A2 Location in patent:Page/Page column 90-91