《2-(2》.pdf

Organic Syntheses, Vol. 83, p. 155-161 (2006); Coll. Vol. 11, p. 46-51 (2009). 2-(2 ,2-DIMETHYLPROPOXY)-2,3-DIHYDRO-1H-INDENE TBDMSCl A. OH OTBDMS imidazole, DMF Me CCHO 3 B. OTBDMS O BiBr , Et SiH 3 3 CH3CN Submitted by Joginder S. Bajwa,1 Kapa Prasad and Oljan Repi. Checked by Sigrid Holle and Alois Fürstner. 1. Procedure A. 2,3-Dihydro-2-tert-butyldimethysiloxy-1H-indene. A flame-dried 500-mL, four-necked round-bottomed flask equipped with a Teflon-coated magnetic stir bar, a pressure-equalizing dropping funnel, a nitrogen inlet, an internal thermometer and a glass stopper is charged successively under nitrogen atmosphere with 2-indanol (13.42 g, 100 mmol), imidazole (8.17 g, 120 mmol) and 60 mL of dry N,N-dimethylformamide (DMF) (Note 1). The mixture is stirred until a clear solution has formed (Note 2). The flask is immersed in an ice bath and a solution of tert-butyldimethylsilyl chloride (16.32 g, 108 mmol) in 40 mL of dry DMF (Note 3) is added over a period of 10 min at such a rate that the reaction temperature remains below 10 °C. The ice-water bath is removed, the mixture is allowed to warm to ambient temperature and stirring is continued for 45 min (Note 4). Deionized water (150 mL) is added slowly via the dropping funnel, causing a slight exotherm (Note 5), followed by the addition of 100 m