5-Hydroxy-2-methylbenzoxazole

Compound 2 (20.0 g, 119.7 mmol) was dissolved in DMF (300 mL), cooled to 0° C. POClCompounds 3 (1.5 g, 10.06 mmol) and HMTA (5.6 g, 40.0 mmol) were added to TFA (100 mL). The mixture was heated to 90 C. for 1 h. After cooled to RT, the reaction mixture was concentrated, purified by prep-HPLC and prep-TLC successively, afforded 5-hydroxy-2-methylbenzo[d]oxazole-4-carbaldehyde (20.0 mg, 1.1%) as yellow solid.j0454j 2-Methyl-1, 3-benzoxazol-5-ol (1.4 g, 9.39 mmol) and [5-(prop-2-en-1-yloxy)pyridin- 2-yl]methanol (1.8 g, 10, 33 mmol, described in US patent 4, 198, 416 1978) reference example 3) were suspended in anhydrous toluene (20 mL), eyanomethylenetributylphosphorane (3.69 mL, 14.08 mmol) added and the reaction heated to 100 C for 4 hours under nitrogen. The reaction was cooled to room temperature and the solvent removed in vacua. Trituration with diethyl ether and heptane (1:1, 10 mL) gave the title compound 1.449 g (52% yield) as a purple solid. SH NMR (250 MHz, DM50) 8.31 (d, J = 2.3 Hz, 1H), 7.55 (d, J = 8.9 Hz, 1H), 7.49 (d, J = 8.4 Hz, 1H), 7.43 (dd, J = 8.6, 2.8 Hz, 1H), 7.29 (d, J = 2.5 Hz, IH), 7.00 (dd, J = 8.9, 2.6 Hz, IH), 6.05 (ddt, J = 17.2, 10.5, 5.2 Hz, 1H), 5.42 (dq, I = 17.3, 1.7 Hz, 1H), 5.29 (dq, I = 10.5, 1.4 Hz, 1H), 5.14 (s, 2H), 4.67 Cdt, J = 5.2, 1.4 Hz, 2H), 2.58 Cs, 3H) Tr(METCRI673) = 1.26 mm, (Est) (M+H)t 297.

Molecular Weight:149.15
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:149.047678466
Monoisotopic Mass:149.047678466
Topological Polar Surface Area:46.3
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes