2-Heptanone, 1-(triphenylphosphoranylidene)- → 2-(6-Hydroxyhexyl)-3-(3-oxo-1-octenyl)cyclopentanol

Participants

Reaction Steps

A mixture of 3-hydroxy-2-(6-hydroxyhexyl)cyclopentanecarbaldehyde (8.6 g.) and hexanoylmethylene triphenylphosphorane (16 g., 0.043 mole) in dry tetrahydrofuran (100 ml.) was heated under reflux for 6 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel. Elution with a 3:2 mixture of petrol (b.p. 40°-60°C.) and ethyl acetate gave 2-(6-hydroxyhexyl)-3-(3-oxo-1-octenyl)cyclopentanol (8 g.), νmax 1660 cm-1, 1620 cm-1 (liquid film).

Provenance & Evidence