Isobutylene oxide → HCID 86653375, compound

Participants

Reaction Conditions

Reaction Steps

Et2O (100 mL) was added to compound B (5.50 g, 26.3 mmol) to form a clear yellow solution. A solution of 1,2-epoxy-2-methylpropane (1.90 g, 26.3 mmol) in Et2O (5 mL) was added dropwise over about 10 seconds, and the mixture was stirred overnight. The mixture was then 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, a solid was collected on a glass frit and washed with Et2O (3×15 mL). The solid was dried under reduced pressure. The dried solid 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 which caused a white crystalline solid to form. The ether solution was cooled to −10° C. overnight. The white solid was then collected and dried under reduced pressure to afford 1.48 g of product C. 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. The combined yield of compound C was 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