p-Toluenesulfonic acid monohydrate → HCID 10678360, compound

Participants

Reaction Steps

To a 5 mL round-bottom flask is added at room temperature p-toluenesulphonic acid monohydrate (0.01 g, 0.053 mmol), methanol (8 mL) and (1R-cis)-4-nitromethyl-2-cyclopentene -acetate as prepared in Example 10 (0.20 g, 1.1 mmol) and the resulting solution is stirred overnight. The crude reaction mixture is loaded on a silica column (32 μm-63 μm) and purified by flash chromatography by eluting with 20% ethyl acetate/hexane. The fractions containing the product (Rf=0.3) are combined and are concentrated in vacuo to give (1R-cis)-4-nitromethyl-2-cyclopenten-1-ol as a clear oil which exhibited the following physical data: MS(CI) m/z=126 [C6H8NO2 +, Loss of H2O followed by rapid protonation]; and [α]D20 =+4.8° (c=0.16, CHCl3).

Provenance & Evidence