Diethyl Ether → HCID 59330258, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0M solution of diisobutylaluminium hydride (115 mL, 0.115 mol) in toluene is added dropwise over a period of 30 mins to a stirred solution of 4,7-dimethyl-3H-isobenzofuran-1-one 4 (18.66 g, 0.115 mol) in anhydrous toluene (250 mL) at −15° C. under nitrogen. Anhydrous diethyl ether (100 mL) is added and the reaction mixture is stirred 4 h at −50° C. The reaction mixture is removed from the cooling bath and diethyl ether (300 mL) is immediately added followed by saturated brine (200 mL). The organic layer is separated and the aqueous layer is re-extracted with diethyl ether (200 mL). The combined organics are dried over sodium sulfate and concentrated in vacuo to yield a cream solid. The solid is dissolved in anhydrous methanol (400 mL) and boron trifluoride diethyl etherate (2.3 mL, 0.018 mol) is added at 0° C. and the solution is stirred for 20 h at RT under nitrogen. The reaction mixture is poured into brine (200 mL) and extracted with petrol 40-60 (2×200 mL). The combined extracts are washed with water (3×100 mL), dried over sodium sulphate, and concentrated in vacuo to yield the product 5 as a yellow oil (17.14 g, 84%): 1H-NMR (300 MHz, CDCl3) δ 7.03 (q, 2H, 3J=7.5 Hz, 4.5 Hz), 6.20 (s, 1H), 5.15 (d, 1H, 3J=13.5 Hz), 4.98 (d, 1H, 3J=13 Hz), 3.42 (s, 3H), 2.31 (s, 3H), 2.20 (s, 3H); 13C-NMR (75 MHz, CDCl3) δ 138.7, 135.3, 130.8, 130.2, 129.1, 128.3, 107.7, 72.2, 54.0, 18.1, 17.5.

Provenance & Evidence