Water → (S)-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde oxime

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Reaction Steps

(R)-2,2,5,5-Tetramethyl-1,3-dioxolane-4-carbaldehyde (16 g, 101 mmol) [Burger, A. Synthesis 1989, (2) 93-97] was dissolved in 1:1 methanol:water (250 mL) and hydroxylamine hydrochloride (7.0 g, 101 mmol), and Na2CO3 (5.4 g, 51 mmol) was added. The reaction was stirred at ambient temperature for 2 hours. The methanol was partially removed in vacuo and the aqueous layer was extracted with CH2Cl2, dried, filtered and concentrated to afford (S)-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde oxime (13 g, 75 mmol, 74% yield) as an amber oil.

Provenance & Evidence