Tetrahydrofuran → HCID 86751987, compound

Participants

Reaction Steps

A mixture of [S-(R*,R*)]-α-(2-methylpropyl)-α-(propen-2-yl)-γ-hydroxymethyl-γ-butyrolactone (682 mg, 3.21 mmol), NaOH (350 mg, 8.75 mmol), THF (40 mL), and H2O (10 mL) is stirred for 19 hours at room temperature. Additional NaOH (114 mg, 2.85 mmol) is added after 16 hours. The mixture is concentrated and the residue taken up into MeOH (43 mL). A solution of sodium periodate (862 mg, 4.03 mmol) and H2O (4.3 mL) is added and the mixture stirred at room temperature for 3 hours. After concentration, the aqueous residue is acidified (HCl) and extracted with CH2Cl2 (3×40 mL). The organic layers are dried (MgSO4), filtered, and concentrated to provide 625 mg (98%) of the title compound as a semi-solid.

Provenance & Evidence