Methanol → HCID 9799463, compound

Participants

Reaction Steps

A mixture of 0.5 ml of a 0.05M solution of 3,5-dimethyl-6-(4-methoxyphenyl)-3,6-dihydro-2H-1,2-oxazine in dichloromethane. 0.5 ml of a 0.75M solution of 3,4-dimethoxybenzaldehyde in dichloromethane, and 0.5 ml of a 0.75M solution of sodium triacetoxyborohydride in dichloromethane was stirred at ambient temperature for 19 h. Methanol (1.0 ml) was added with stirring and the mixture applied to a methanol washed 500 mg Isolute SCX cartridge (Jones Chromatography). The absorbent was washed with methanol (2.5 ml) and then eluted with 2M ammonia in methanol (2.5 ml). The eluate was concentrated to dryness using a centrifugal evaporator and the residue dissolved in chloroform (2 ml) and added to methylisocyanate-polystyrene (loading 1.0 meq/g, 100 mg). This suspension was shaken gently for 19 h, then filtered and resin washed with chloroform (2×2 ml). Removal of the solvent from the combined filtrates by centrifugal evaporation gave 3,5-dimethyl-2-(3,4-dimethoxybenzyl)-6-(4-methoxyphenyl)-3,6-dihydro-2H-1,2-oxazine. 1H NMR (CDCl3) δ 1.23(3H, d), 1.49(3H, s), 3.39(1H, m), 3.62(1H, d), 3.70(3H, s), 3.79(3H, s), 3.83(3H, s), 4.05(1H, d), 4.92(1H, s), 5.61 (1H, d), 6.64 (3 H, m),6.81 (2H, d), 7.22 (2H, d).

Provenance & Evidence