Isobutylene oxide → HCID 86653375, compound

Participants

Reaction Conditions

Reaction Steps

Et2O (100 mL) was added to compound 2 (5.50 g, 26.3 mmol) to form a clear yellow solution. An Et2O (5 mL) solution of 1,2-epoxy-2-methylpropane (1.90 g, 26.3 mmol) was added dropwise over about 10 seconds, and the mixture was stirred overnight. The next day the mixture was cooled to −80° C. and trifluoromethanesulfonic anhydride (7.42 g, 26.3 mmol) was added dropwise. The mixture was warmed to ambient temperature over 1 hour. A thick suspension formed. After stirring for an additional hour, the solid was collected on a glass frit and washed with Et2O (3×15 mL). The solid was dried under reduced pressure. This was then extracted with CH2Cl2 (60 mL) and filtered through diatomaceous earth. The filter cake was washed with CH2Cl2 (2×30 mL). The combined CH2Cl2 extracts were evaporated to an oil and Et2O (15 mL) was added to cause a white crystalline solid to form. The solution was cooled to −10° C. overnight. The solid was then collected and dried under reduced pressure to afford 1.48 g of product. To obtain additional product the filter cake was loaded into a thimble. This was placed in a Soxhlet extractor and the solid was extracted with hot CH2Cl2 overnight. The resulting CH2Cl2 extract was evaporated and Et2O (10 mL) was added to afford additional product as off-white crystals. Total yield: 3.28 g, 30.6%. 1H NMR(C6D6): δ 7.21 (1H, d), 7.02 (2H, m), 2.47 (4H, q), 2.39 (1H, m), 1.11 (6H, t), 1.01 (6H, d).

Provenance & Evidence