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Chemistry 30A3 Fall 2011 Labs Dr. Troendle 20

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 20 - solid The...

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Chemical Biology 3OA3, September 2009 Page 20 Sample Write Up from a Research Notebook : Attempted Reaction of 8,8-Dimethylbicyclo[5.1.0]octa-3, 5-dien-2-one with Methyl Lithium Procedure The methyl lithium solution was added dropwise to a stirred solution of the ketone in ether at -78 o C under Ar. The mixture was kept at -78 o C for 1 h. after addition, then warmed to 0 o C and H 2 O (3 mL) was added through a syringe. The ether layer was separated, and the water layer was washed with Et 2 O (2 x 3 mL). The combined ether layers were dried (K 2 CO 3 ) and ether was evaporated to give an oily
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Unformatted text preview: solid. The solid was recryst. from pentane, then sublimed (50 o C/10 mm) to give a colourless solid. Results Yield 45 mg; 45/164 = 0.274 mmol; 0.274/0.5 = 55% mp 61-64 o C 1 H nmr (CS 2 , 60 MHz) δ 5.95 (t, J=7 Hz, 1H, C=CH ), 5.50 (m, 3H, C=CH ), 1.70 (d, J=9 Hz, 1H, cyclopropyl-H ), 1.30 (m, 2H, OH and cyclopropyl-H ), 1.30 (s, 3H, CH 3 ), 1.19 (s, 3H, CH 3 ), 1.08 (s, 3H, CH 3 ). Conclusion Sample appears pure (mp and 1 H nmr). Seems to be desired tertiary alcohol. Need infrared and C/H analysis. OK to try next step. Stereochemistry?...
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