Ammonium Chloride → HCID 68636260, compound

Participants

Reaction Conditions

Reaction Steps

At 20° C., a solution of lithium diisopropylamine (9.3 ml, 2M in THF/heptane) was treated dropwise within 10 min. with a solution of allylmagnesium chloride (15 ml, 2 M in THF). The resulting mixture was heated at 33° C., treated dropwise with a solution of ethyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (6 g, 27 mmol) in THF (7 ml), stirred at 20° C. for 1 h and at 40° C. for 24 h, treated with a mixture of allylmagnesium chloride (15 ml, 2 M in THF) and lithium diisopropylamine (9.3 ml, 2M in THF/heptane), stirred at 30° C. for 2 h, poured into a mixture of a saturated aqueous solution of NH4Cl (100 ml) and ice (115 g), and diluted with MTBE (200 ml). The organic phase was washed with 10% aqueous HCl (80 ml), with a saturated aqueous solution of NaHCO3 (80 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4) and concentrated. FC (SiO2, hexane/MTBE 100:1 to 90:10) of the crude product (8.3 g) gave (E)-1-(7-methylspiro[4.5]dec-7-en-6-yl)but-2-en-1-one and (E)-1-(7-methylspiro[4.5]dec-6-en-6-yl)but-2-en-1-one (1 g, 17%).

Provenance & Evidence