Dimethylformamide dimethyl acetal → HCID 44551319, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of compound 12 (2.3 g, 9.4 mmol) in dry DMF (15 mL) was added N,N-dimethylformamide dimethyl acetal (DMF·DMA) (6.0 g, 24.5 mmol). After the reaction mixture was heated at 140° C. for 16 h, the dark red solution was cooled to 0° C. and added rapidly to a stirred solution of NaIO4 (10.5 g, 49 mmol) in H2O/DMF (4:1, 25 mL) at 0° C. After 8 h of stirring, the brown solution was filtered, and the reaction flask was rinsed with toluene/EtOAc (1:1, 30 mL) and again filtered. The filtrate was washed with saturated aqueous NaCl solution (45 mL) and extracted with EtOAc (2×45 mL). The organic phase was dried (Na2SO4) and concentrated, and the residue was purified by flash chromatography (hexane/EtOAc 3:1) to afford aldehyde 13 (1.3 g, 54%): Rf0.22 (hexane/EtOAc 3:1); 1H NMR (CDCl3) δ 4.09 (s, 3H), 7.38 (s, 1H), 8.43 (s, 1H), 10.50 (s, 1H); 13C NMR (CDCl3) δ 57.4, 110.5, 116.8, 130.3, 132.6, 142.3, 160.5, 187.7; ESI-HRMS [M-H]−C8H579BrNO4 calcd for m/z 257.9402, found 257.9407.

Provenance & Evidence