Diazomethane → Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate

Participants

Reaction Steps

A solution of diazomethane (0.327 g.) in dry diethyl ether (10 ml.) was added to a solution of 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoic acid (0.4 g.) [prepared as described in Example 1] in dry diethyl ether (10 ml.). The resulting solution was allowed to stand at ambient temperature for 18 hours, during which time a solid precipitated. The solid was removed by filtration and the filtrate evaporated. The remaining traces of ether were removed from the residue by pumping under high vacuum to give methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (0.3 g., 72%). (Found: C, 70.8; H, 10.6. C21H38O4 requires C, 71.25; H, 10.72%) νmax 1730 cm-1, 980 cm-1 (liquid film). N.M.R. (approximately 10% solution in deuterochloroform) 0.92δ (triplet J=5c/s, terminal CH3) 1.7, 1.4δ (overlapping multiplets, cyclic and chain CH2), 2.38δ (triplet J=6.5c/s, CH2C=0), 2.70δ (broad singlet, --OH), 3.76δ (singlet --COOCH3), 4.32, 4.15 and 4.00δ (overlapping multiplets, cis and trans ##EQU7## 5.62δ (multiplet, ##EQU8##

Provenance & Evidence