2-Methyl-2-phenyl-1,3-dioxolane → 2-Phenyl-4-penten-2-ol

Participants

Reaction Conditions

Reaction Steps

2-Methyl-2-phenyl-1,3-dioxolane (0.5 g, 3 mmol), sodium dodecyl sulfate (0.2 g, 0.7 mmol) and a stir bar were added to the inside of a PDMS thimble. p-Toluene sulfonic acid monohydrate (0.145 g, 0.8 mmol) dissolved in 4 mL water was added to the inside of the PDMS thimble followed by 2 mL of hexanes. The reaction was stirred at 25° C. for 5 hours. Hexanes (5 mL) and 24 mL of 1 M allyl magnesiumbromide (3.49 g, 24 mmol) in diethyl ether was added to the outside of the PDMS thimble and the reaction was stirred for 14 hours. Water (5 mL) was added. The PDMS thimble was swelled with 20 mL hexanes and 2×20 mL diethyl ether and the organics were combined and dried over MgSO4. The product was purified by flash chromatography eluting with 100% hexanes initially, increasing to 1:49 ethyl acetate:hexanes to yield a colorless oil (0.39 g, 79% yield). 1H NMR (CDCl3): δ 1.54 (s, 3H), 2.09 (s, 1H), 2.49 (dd, J=13.8, 8.4 Hz, 1H), 2.68 (dd, J=13.5, 6.3 Hz, 1H), 5.09-5.16 (m, 2H), 5.55-5.66 (m, 1H), 7.21-7.26 (m, 1H), 7.31-7.36 (m, 2H), 7.41-7.45 (m, 2H). 13C NMR (CDCl3): δ 29.86, 48.42, 73.58, 119.43, 124.72, 126.57, 128.13, 133.63, 147.59.

Provenance & Evidence