Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → HCID 56597854, compound

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Reaction Conditions

Reaction Steps

23B (0.16 g, 0.53 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.11 g, 0.50 mmol) were mixed together in a microwave vial together with toluene (3 mL). The mixture was heated in a microwave oven at 140° C. for 30 min. The solvent was removed by evaporation. The product was purified by preparative chromatography on a Kromasil C8 column eluting with acetonitrile and 0.1 M NH4OAc. The combined fractions were concentrated and the aqueous solution was pH adjusted to pH 9 with 1M NaOH. The mixture was extracted with EtOAc and the organic layer was dried over Na2SO4. The solvent was removed by evaporation. There was obtained 24 mg (10%) of the product as a foam. 1H NMR (400 MHz, CDCl3): δ 2.08 (s, 3H), 2.32-2.47 (m, 4H), 3.37-3.54 (m, 4H), 3.62 (s, 2H), 4.29-4.40 (m, 1H), 4.59-4.70 (m, 1H), 4.71-4.82 (m, 1H), 5.02-5.19 (m, 2H), 6.74 (d, 2H), 7.26 (d, 2H), 7.49-7.64 (m, 3H), 8.16 (d, 2H), MS (APCI+) m/z 462 [M+H]+, LC purity: 93%.

Provenance & Evidence