Ethyl bromoacetate → HCID 136386266, compound

Participants

Reaction Conditions

Reaction Steps

Compound 10 (2.21 g, 10 mmol) and Na2CO3 (2.12 g, 20 mmol) were suspended in dry DMF, and the mixture was warmed to 80° C. with stirring. After 1 h the heating was terminated, and the reaction mixture was cooled to 0° C. and ethyl bromoacetate (1.22 mL, 11 mmol) was added dropwise for 1 h. The stirring was continued for an additional 2 h. The reaction mixture was filtered and the solid was washed with DCM. The filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography ((DCM/MeOH; 9.5/0.5) to obtain 11 as a white solid: yield 0.77 g (25%); MS(+ESI): m/z 308 [M+H]+; 1H NMR (400 MHz, CDCl3): δ11.99 (s, 1H), 8.50 (s, 1H), 7.71 (s, 1H), 4.80 (s, 2H), 4.26 (q, 2H, J=6.8 Hz), 2.70 (septet, 1H, J=6.8 Hz), 1.31 (t, 3H, J=6.8 Hz), 1.28 (d, 6H, J=6.8 Hz); 13C NMR (400 MHz, CDCl3): δ178.3, 166.9, 155.4, 148.5, 147.6, 139.2, 120.8, 62.3, 44.5, 36.5, 18.9, 14.1.

Provenance & Evidence