Sodium Hydroxide → HCID 67797893, compound

Participants

Reaction Steps

A solution of 28.2 g (0.0597 mol) of methyl (Z)-(2S,3S,4R)-7-[4-(1,1'-biphenyl-4-ylmethoxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-4-heptenoate, 433 ml of methanol and 172.8 ml (0.173 mmol) of 1N sodium hydroxide is stirred at 45° C. for two h and at room temperature for 11/2 h. The solvent is evaporated, the residue is taken up in water and extracted twice with ethyl ether. The aqueous layer is adjusted to pH 5.5 and extracted with ethyl acetate (3×10 ml). The combined extracts are washed with brine, dried (MgSO4), evaporated and the residue is crystallized from methylene chloride and ether to give (Z)-(2S,3S,4R)-7-[4-(1,1'-biphenyl-4-ylmethoxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-4-heptenoic acid, having mp. 96°-98° C. and [α]D 25=+98.58 (MeOH).

Provenance & Evidence