HCID 129792804, compound → HCID 131710381, compound

Participants

Reaction Steps

2-Ferrocenyl-2-(3-hydroxypropyl)tetrahydrofuran (II), 20.5 g (0.065 mole), was dissolved in 100 ml of trifluoroacetic acid at 25°C with external cooling (in an ice bath). After 5 hours about half of the trifluoroacetic acid was removed under reduced pressure at 25°C. The residue was dissolved in 200 ml of tetrahydrofuran (THF). Then 100 ml of 6N NaOH was added with cooling and the mixture was stirred overnight. The THF phase was separated and the THF removed under reduced pressure. The product crystallized out in the form of plates. The plates were suspended in 500 ml of water, filtered and then washed twice on the filter with 50 ml portions of water. The wet cake was removed from the filter, triturated with 50 ml of ether and then filtered to give 11.0 grams of V, mp 85°-88°C. An additional 2.0 g of material, mp 85°-88°C, was recovered from the liquid phases to give a total yield of 4-ferrocenyl-3heptene-1,7-diol of 13.0 g (63% yield).

Provenance & Evidence