Benzoic Acid → (4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

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Reaction Steps

To a stirred solution of triphenylphosphine (560 mg, 2.134 mmol) and benzoic acid (261 mg, 2.134 mmol) under nitrogen in anhydrous THF (8.0 mL) was added (4aR,7R,8aS)-2-phenylhexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (500 mg, 2.134 mmol), then DIAD (0.41 mL, 428 mg, 2.116 mmol) dropwise over 10 minutes. After stirring at room temperature for 1 hour, the mixture was concentrated under reduced pressure. The resultant oil was dissolved in DCM, then loaded directly onto a Biotage™ 50 g (2×25 g in series) silica gel cartridge and eluted with 0-100% EtOAc in 1:1 Hexane/DCM over 25 column volumes. The product fractions were combined and concentrated under reduced pressure to provide the desired product as a white solid. LC-MS: calculated for C20H20O5 340.13, observed m/e: 341.13 (M+H)+ (Rt 2.21/4 min).

Provenance & Evidence