1-(Cyclopropylmethoxy)-3-ethynylbenzene synthesis

Yield:918483-34-8 84%

Reaction Conditions:

with caesium carbonate;sodium iodide in acetone at 20;Heating / reflux;

Steps:

68

EXAMPLE 68 Preparation of 1-(cyclopropylmethoxy)-3-ethynylbenzene To a solution of 3-ethynylphenol (1.18 g, 10.0 mmol) in acetone (30 mL) is added (bromomethyl)cyclopropane (1.02 mL, 10.0 mmol), sodium iodide (0.75 g, 5.0 mmol) and Cs₂CO₃ (6.52 g, 20.0 mmol) at room temperature. After refluxing over night, the reaction mixture is cooled, diluted with Et₂O (300 mL) and pass through a thin layer of silica gel. The solution is concentrated. The resultant residue is purified by chromatography (silica gel, EtOAc/hexane: 1/99) to give the title compound (1.45 g, 84%) as an oil. MS(+) APPI: 173 (M+H)⁺.

References:

US2007/4730,2007,A1 Location in patent:Page/Page column 18-19