US 8,410,314 B1 · Method of synthesis

Abstract

Described is a method of synthesizing 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one by reacting 3-(5-ethoxyhept-1-yl)cyclopentene with dichloroketene. The resulting reaction products are reacted with acetic acid and zinc to produce 4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-6-one and 4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one, which are reacted with trimethylsulfonium iodide to produce 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2′-oxirane] and 4-(5-ethoxyhept-1-yl)spiro-[bicyclo-[3.2.0] heptane-6,2′-oxirane]. Lithium iodide is reacted with 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2′-oxirane] and 4-(5-ethoxyhept-1-yl)spiro-[bicyclo-[3.2.0]heptane-6,2′-oxirane] to produce 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one. A method of synthesizing 6-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-3-one is also described.

Claims10

Dependent claims

A method of synthesizing a compound, the method comprising:

reacting 3-(5-ethoxyhept-1-yl)cyclopentene with dichloroketene to form a first mixture comprising 7,7-dichloro-4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-6-one and 6,6-dichloro-4-(5-eth-oxyhept-1-yl)bicyclo[3.2.0]heptan-7-one;
reacting the first mixture with acetic acid and zinc to form a second mixture comprising 4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-6-one and 4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one;
reacting the second mixture with trimethylsulfonium iodide to form a third mixture comprising 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2′-oxirane] and 4-(5-ethoxyhept-1-yl)-spiro-[bicyclo-[3.2.0]heptane-6,2′-oxirane];
and
reacting the third mixture with lithium iodide to form 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one.

2 more elements

Dependencies are inferred from the claim text.

Method of synthesis

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Method of synthesis

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Abstract

Claims10