Cyanoacetic acid → HCID 69607371, compound

Participants

Reaction Steps

To PCl15 (854 g, 4.1 mol) in 10 mL anhydrous CH2Cl2 was added cyanoacetic acid (348 g, 4.1 mmol). The reaction mixture was refluxed for 0.5 h, and then 4-(4-Allyloxyphenyl)-2-amino-5-methyl-thiophene-3-carboxylic acid ethyl ester from Example 29B (1.0 g, 3.1 mmol) in 5 ml anhydrous CH2Cl2 was added dropwise at room temperature. The reaction mixture was refluxed for 1 h and cooled to room temperature, and then saturated aq. Na2CO3 was added until pH=7. The organic layer was washed with brine, dried over MgSO4, concentrated in vacuo to give the titled compound (1.2 g, 100% yield) as a pale yellow oil which was pure enough to used in next step. 1H NMR (300 MHz, DMSO-d6) δ 11.15 (s, 1H), 7.07 (d, 2H, J=9.0 Hz), 6.97 (d, 2H, J=9.0 Hz), 6.05 (m, 1H), 5.44, 5.38, 5.28, 5.25 (4d, 2H, J=3.0 Hz), 4.60 (d, 2H, J=6.0 Hz), 4.25 (s, 2H), 3.97 (q, 2H, J=6.0 Hz), 2.12 (s, 3H), 0.84 (t, 3H, J=6.0 Hz). MS (ESI) m/e 385 (M+H)+, 383 (M−H)−.

Provenance & Evidence