(3-Hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanone → 3-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-benzaldehyde

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Reaction Steps

A mixture of (3-hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanone (1.9 g, 3.52 mmol), pyridinium chlorochromate (1.14 g, 5.28 mmol), and dried celite (1 g) in dichloromethane (20 ml) was stirred for 1 hr. at room temperature. The mixture was then filtered through a short silica gel pad and the pad was washed with EA. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 1.75 g (74%) of a pale yellow syrup. 1H NMR (200 MHz, CDCl3) δ 1.19 (6H, d, J=7.4 Hz), 2.88 (1H, m), 3.79 (3H, s), 3.83 (3H, s), 5.29 (2H, s), 5.45 (2H, s), 6.77-6.95 (4H, m), 7.28-7.42 (4H, m), 7.65 (1H, m), 8.11-8.28 (3H, m), 10.03 (1H, s).

Provenance & Evidence