1-Bromo-3-methylbutane → HCID 68874755, compound

Participants

Reaction Steps

To a solution of Example 155A (15 g. 77.2 mmol) and hexamethylphosphoric triamide (14.8 mL, 77.2 mmol) in 200 mL anhydrous tetrahydrofuran was added 2 M lithium diisopropyl amide (45 mL, 90 mmol) while maintaining the temperature below −70° C. After 30 minutes at −78° C., 1-bromo-3-methylbutane (10.6 mL, 85 mmol) was added and the reaction stirred for 16 hours at room temperature. Most of the solvent was removed under vacuum and the residue partitioned between ethyl acetate and 1 N HCl. The crude product was purified on silica using 5% ethyl acetate in hexanes to give the product as a colorless oil (18.6 g, 92%). 1H NMR (300 MHz, CDCl3) δ ppm 0.86 (d, J=5.15 Hz, 3 H) 0.88 (d, J=5.15 Hz, 3 H) 1.04 (m, 2 H) 1.51 (m, 1 H) 1.51 (s, 3 H) 1.88 (ddd, J=13.33, 10.57, 6.25 Hz, 1 H) 2.02 (m, 1 H) 3.64 (s, 3 H) 3.79 (s, 3 H) 6.85 (m, 2 H) 7.23 (m, 2 H).

Provenance & Evidence