Triphenylphosphine → 3-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazole

Participants

Reaction Steps

To a solution of triphenylphosphine (161 mg, 0.615 mmol) in dry THF (2.5 mL) is added DEAD (0.097 mL, 0.615 mmol). The solution is stirred at rt for 1 h before (2,2-dimethyl-5-nitro-[1,3]dioxan-5-yl)-methanol (118 mg, 0.615 mmol) and 2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenol (150 mg, 0.410 mmol) is added. Stirring is continued for 7 days. The formed precipitate is collected, washed with isopropanol and dried under high vacuum to give 3-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazole (90 mg) as an almost colourless solid; LC-MS: tR=1.30 min, [M+1]+=540.28; 1H NMR (CDCl3): δ 7.77 (s, 2H), 4.50 (d, J=12.9 Hz, 2H), 4.29-4.21 (m, 4H), 3.10 (dd, J=6.4, 18.8 Hz, 1H), 2.93 (d, J=18.8 Hz, 1H), 2.43 (s, 3H), 2.28 (s, 6H), 2.00-1.91 (m, 2H), 1.48 (s, 3H), 1.45 (s, 3H), 1.15 (s, 3H), 0.76 (s, 3H).

Provenance & Evidence