2-[[3-[Hydroxymethyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]-4-fluoro-1-phenylmethoxy-benzene → 2-[[3-Carboxy-7-oxabicyclo[2.2.1]hept-2-yl]methyl]-4-fluoro-1-phenylmethoxybenzene

Participants

Reaction Steps

To a solution of [1S-(1α, 2α, 3α, 4α)]-2-[[3-[hydroxymethyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]-4-fluoro-1-phenylmethoxy-benzene (0.812 g, 2.37 mmol) in acetone (20 mL) was added Jones reagent (1 mL) (The Jones reagent was prepared by dissolving 534 mg of Chromium oxide in 0.46 mL of acid sulphuric concentrated and 1.54 mL of water) and the resulting mixture was stirred for 10 min. Then, more Jones reagent (1 mL) was added and the mixture was stirred for 1 h. After, 2-propanol (0.6 mL) was added and the reaction was stirred for 5 min. Then the reaction was stopped, the chromium salts were filtered and the solvent was evaporated under vacuum. The crude product was partitioned between chloroform (30 mL) and 2 M HCl (15 mL). The organic phase was separated; it was washed with brine (15 mL), dried (Na2SO4), filtered and the solvent was evaporated “under vacuum” to give the titled compound as a dark solid which was used in the next step without any additional purification. 1H-NMR (CDCl3, 300 MHz) δ 7.35 (m, 5H, ArH), 6.86 (m, 3H, ArH), 5.05 (s, 2H, —OCH2Ph), 4.84 (bs, 1H, —CH—O—), 4.33 (bs, 1H, —CH—O—), 2.87 (m, 2H, —CH—), 2.57 (m, 2H, —CH2—), 1.72 (m, 2H, —CH2—CH2—), 1.34 (m, 2H, —CH2—CH2—).

Provenance & Evidence