One-Pot Synthesis of 3-Hydroxymaleic Anhydrides by Cyclization of 1,1-Bis(trimethylsilyloxy)ketene Acetals with Oxalyl Chloride

Abstract

Functionalized 3-hydroxymaleic anhydrides were prepared by cyclization of 1,1-bis(trimethylsilyloxy)ketene acetals with oxalyl chloride.

Key words

anhydrides - cyclizations - ketene acetals - oxalyl chloride - silyl enol ethers

References

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16

To a CH₂Cl₂ solution (17.8 mL) of oxalyl chloride (0.20 mL, 2.3 mmol) and 1a (0.50 g, 1.8 mmol) was added a CH₂Cl₂ solution (5 mL) of TMSOTf (0.16 mL, 0.9 mmol) at 78 °C. The temperature of the solution was allowed to rise to 20 °C during 12 h. After stirring for 3 h at 20 °C, an aq solution of HCl (10%) was added. The organic and the aqueous layer were separated and the latter was extracted three times with CH₂Cl₂. The combined organic layers were dried (Na₂SO₄), filtered and the solvent of the filtrate was removed in vacuo. The residue was purified by chromatography (silica gel, hexane-EtOAc) to give 3a as a yellow solid (240 mg, 70%), mp 164 °C. ¹H NMR (300 MHz, CDCl₃): δ = 7.42-7.50 (m, 3 H, Ar), 8.05-8.08 (m, 2 H, Ar). ¹³C NMR (75 MHz, CDCl₃): δ = 112.0 (C), 126.9 (C), 128.8 (CH), 129.1 (CH), 130.3 (CH), 149.4 (C), 163.4 (C), 163.5 (C). IR (neat): 3244 (s), 3123 (w), 1840 (s), 1760 (s), 1673 (s), 1393 (s), 1262 (s), 939 (s), 762 (s) cm^-1. MS (EI, 70 eV): m/z (%) = 190 (43) [M⁺], 162 (100), 145 (22), 118 (27), 105 (15), 89 (81), 77 (8). Anal. Calcd for C₁₀H₆O₄: C, 63.16; H, 3.18. Found: C, 62.87; H, 3.63.