Hydrogen Peroxide → (2R)-2-(Hydroxymethyl)-7-octenoic acid

Participants

Reaction Steps

A 0.05 M solution of (4S)-3-[(2R)-2-(hydroxymethyl)-7-octenoyl]-4-benzyl-1,3-oxazolidin-2-one (2.55 g, 7.70 mmol) in a 4:1 mixture of THF and H2O was treated with 30% H2O2 (4.0 mL, 30.82 mmol), followed by LiOH (0.70 g, 15.41 mmol) at 0° C. The resulting mixture was stirred and allowed to warm to room temperature overnight. THF was then removed under vacuum. The residue was washed with dichloromethane (50 mL×2) to remove (S)-4-benzyl-oxazolidin-2-one. The desired product was isolated by EtOAc extraction of the acidified (pH 1˜2) aqueous phase. No further purification was required. Standing under high vacuum yielded the title compound. MH+173.

Provenance & Evidence