Sodium hydride → 8-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Participants

Reaction Steps

When the bridging group n is --OCH2 --, 1,4-dioxaspiro[4.5]decan-8-ol (the preparation of which was previously described) is treated with sodium hydride and reacted with an appropriately substituted or unsubstituted phenylmethyl bromide, for example, 3-trifluoromethylphenylmethyl bromide, affording the corresponding 8-phenylmethoxy-1,4-dioxaspiro[4.5]decane. The 1,4-dioxaspiro functional group is then cleaved from the so-prepared molecule with acetic acid and water, affording the corresponding 4-phenylmethoxycyclohexanone, which is in turn reacted with cyanoguanidine, yielding the targeted 2,4-diamino-6-phenylmethoxy-5,6,7,8-tetrahydroquinazoline. Example 11 provides a detailed description of how this reaction is conducted.

Provenance & Evidence