2-Methyl-3-butyn-2-ol → HCID 54381551, compound

Participants

Reaction Steps

A mixture of 118 mg (0.52 mmole) of 10-chloromethyl-6-methyl-5,10-undecadien-7-yn-2-one (produced in accordance with Example III), 46 mg (0.55 mmole) of 2-methyl-3-butyn-2-ol (purchased from Aldrich Chemical Co., Milwaukee, Wis.), 125 mg (0.90 mmole) of anhydrous potassium carbonate, 12 mg (0.12 mmole) of cuprous chloride, and 13 mg (0.057 mmole) of benzyltriethylammonium chloride in 0.75 mL of acetonitrile (HPLC-grade, purchased from Aldrich Chemical Co., Milwaukee, Wis.) was stirred vigorously at room temperature for 25 hours, during which time the mixture was maintained under an atmosphere of nitrogen. Isolation of the product as described in the procedure of Example III afforded, after removal of the volatile organic solvents at reduced pressure, 109 mg (77% yield) of the named C-18 ketone. The proton NMR spectrum of this compound exhibited a singlet at δ1.50 [6H's, C(CH3)2 ], a singlet at δ1.77 (CH3 bonded to C-6), a singlet at δ2.12 (CH3C=O), and two singlets at δ2.97 and 3.04 (4H's, hydrogens bonded to C-11 and C-9).

Provenance & Evidence