1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68723174, compound

Participants

Reaction Conditions

Reaction Steps

A solution of a 30:70 mixture of cis-/trans-ethyl 9-acetoxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (2.7 g, 9.6 mmol) in DBU (15 ml, 97 mmol) was stirred for 4 d at 20° C. The reaction mixture was poured into cold 2N aqueous HCl (50 ml), and extracted twice with MTBE (50 ml). The combined organic phases were washed with 2N aqueous HCl (30 ml), with water (40 ml), with a saturated aqueous solution of NaCl (40 ml), dried (MgSO4), and concentrated. FC (250 g SiO2, pentane/Et2O 100:1) of the crude product (1.8 g) gave methyl 7-methylspiro[4.5]deca-6,8-diene-6-carboxylate (0.54 g, 25%).

Provenance & Evidence