Synthesis of 1-Methylcyclopropyl Aryl Ethers from Phenols Using an Alkenylation-Cyclopropanation Sequence.

1-Methylcyclopropyl aryl ethers (McPAEs) can be viewed as cyclized derivatives of their O-tert-butyl counterparts. Although these compounds can find use in medicinal chemistry, they are much less represented in the literature than their aryl cyclopropyl ether analogues. McPAEs are generally prepared via an SNAr reaction using 1-methylcyclopropanol. However, this method works exclusively with highly deactivated arenes. We report herein a two-step sequence to access McPAEs consisting of the 1-methylvinylation of phenols followed by cyclopropanation of the corresponding 1-methylvinyl aryl ethers. Isomeric mono- and dimethyl analogues were also prepared using this sequence.