Sodium Hydroxide → (2E)-4-(tert-butoxy)-4-oxobut-2-enoic acid

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Reaction Steps

4-1 (340 mg, 1.7 mmol) was stirred for 1 h at rt with a solution comprised of 4 mL THF, and 4 mL of a solution containing 1 M NaOH and 1 M LiCl. The resulting mixture was acidified to pH 3-4 with 1 M KHSO4 and extracted twice with 30 mL of EtOAc. The extract was washed with 30 mL of brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting material was subjected to silica gel flash chromatography using a gradient of 5–10% methanol in DCM to yield 240 mg (82% yield) of 4-2.

Provenance & Evidence