Sodium Hydroxide → HCID 68723299, compound

Participants

Reaction Steps

At 20° C. under N2, a suspension of anhydrous ZnCl2 (0.31 g, 2.29 mmol) in Et2O (1.5 ml) was treated with 1,3-pentadiene (65% pure, 3.34 ml, 22.9 mmol) then with a solution of 1-cyclopropylidenepropan-2-one (0.44 g, 4.58 mmol) in Et2O (1,5 ml). After 24 h stirring, the resulting mixture treated with 6N aq. NaOH (3.1 ml) and the aqueous phase extracted three time with Et2O. The combined organic phases were washed twice with a saturated aqueous solution of NH4Cl, once with a saturated aqueous solution of NaCl, dried (MgSO4), and concentrated. FC (100 g SiO2, pentane/Et2O 10:0.5) of the crude product (1.12 g) gave rel-(4R,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (279 mg, 36%).

Provenance & Evidence