Hydrochloric Acid → 5-(1-Methoxy-2-methylpropan-2-yl)-1,2-oxazol-3-amine

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Reaction Steps

A solution of hydroxylamine sulfate (976 mg, 5.947 mmol) in water (4 mL) is added to a stirred solution of 5-methoxy-4,4-dimethyl-3-oxo-pentanenitrile (1.678 g, 10.812 mmol) and sodium hydroxide (490.3 mg, 11.89 mmol) in water (13 mL). The reaction mixture is heated to reflux over 30 minutes and kept at reflux for 1 hour. After cooling, 37% HCl aqueous solution (0.8 mL, 9.73 mmol) is added and the mixture is heated to reflux for 20 minutes. After cooling, the mixture's pH is adjusted to ˜12 by adding 40% sodium hydroxide aqueous solution. The mixture is extracted with methylene chloride 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 171 [M+H+].

Provenance & Evidence