Diiodomethane → 2,2,5a-Trimethyloctahydro-3,6-methanocyclopropa[a]inden-1b(1H)-ol

Participants

Reaction Steps

A suspension of 19 g of zinc dust and 29 g of cuprous chloride powder in 125 ml of ether are stirred under reflux for thirty minutes. Diiodomethane (14.8 ml) is added dropwise over a twenty minute period. No external heat is required and the addition is carried out at a rate sufficient to maintain reflux (36°-41° C). 1.5 g of the product produced in Example VI, 9,10,10-trimethyl-tricyclo-(4.3.1.04,9)-dec-2-en-1-ol, is then added dropwise over a twenty minute period without external heating. Reflux is maintained (41°-46° C) throughout addition of the dec-2-en-1-ol. The reaction mass is refluxed daily for 8.5 hours for 5 days (42 hours in all) adding more ether and diiodomethane as required. The course of the reaction is followed by GLC (20 feet × 1/4 inch 5% SE-30 prog. 100°-220° C at [4°/min.).

Provenance & Evidence