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US 6,072,094 AGranted
Efficient synthesis of cyclopropylacetylene
AssigneeMerck & Co., Inc.
InventorsSandor Karady, Benjamin Marcune
Life of this patent
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Abstract
An efficient and facile process for the preparation of cyclopropylacetylene from thioanisole and cyclopropyl substituted ketones or aldehydes is disclosed.
Claims7
A process for the preparation of cyclopropyl acetylene (CPA), represented by formula I:
- ##STR13## which comprises reacting a compound represented by formula II:
- ##STR14## wherein X is H, halo, CF.sub.3, or C.sub.1-6 alkyl;
- in the presence of a base and a silylating agent, to a compound represented by formula III:
- ##STR15## wherein each R is independently a C.sub.1-6 alkyl and X is described above;
- reacting a compound of formula III with a compound of formula IV:
- ##STR16## in the presence of a base to yield a vinyl thioether, represented by formula V and VI:
- ##STR17## reacting a compound of formula V and VI in the presence of potassium diaminopropane (KAPA) to yield cyclopropyl acetylene.
4 more elements
A process for the preparation of cyclopropyl acetylene (CPA), represented by formula I:
- ##STR18## which comprises reacting a compound of formula II:
- ##STR19## wherein X is H, halo, CF.sub.3, or C.sub.1-6 alkyl;
- in the presence of BuLi and TMSCl, to a compound represented by formula III:
- ##STR20## wherein each R is independently a C.sub.1 alkyl and X is described above;
- reacting a compound of formula III with a cyclopropyl carboxaldehyde, represented by formula IV:
- ##STR21## in the presence of BuLi to yield vinyl thioethers, represented by formula V and VI:
- ##STR22## reacting a compound of formula V and VI in the presence of potassium diaminopropane (KAPA) to yield cyclopropyl acetylene.
4 more elements
Dependencies are inferred from the claim text.