Iodine → 1,2,3,4-Tetrahydro-1,4a,9b-trimethyl-1,4methanodibenzofuran-8-carbaldehyde

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Reaction Steps

13.76 g (44.8 mmol) of 8-bromo-THTMDBF obtained in Example 2 were added dropwise into a three-necked flask under nitrogen containing 1.31 g of magnesium and an iodine crystal in 5 ml of tetrahydrofuran, and the mixture was maintained under reflux for 2 h, 30 min. After the magnesium was filtered off, the reaction medium was poured into ice-cold water, acidified to pH 1 with concentrated hydrochloric acid and extracted with ether. The organic phase was washed with water, dried over magnesium sulfate, filtered and evaporated to yield 8.47 g (74%) of the expected compound, melting at 144.7° C.; αD =-7° (c=1, chloroform).

Provenance & Evidence