Reaction #554575
ord-0c3f2de7ecae4ff483c3d51b7ba30cc8
Reaction equation
15a
Methyl 6-trityloxy-hexanoate
15b
Methyl-9-trityloxy-nonanoate
15c
Methyl-12-trityloxy-dodecanoate
→
12-trityloxydodecanoic acid
12-Trityloxy-dodecanoic acid
Reactants
Reagents
None
Conditions
Detailed conditions
See reaction.notes.procedure_details.
Workup
- 1Temperatureduring which the pH was maintained above 4
- 2OtherAfter recrystallization for solid product or flash chromatography for oil products, 6-trityloxyhexanoic acid 16a, 9-trityloxynonanoic acid 16b
Procedure
Hydrolysis of the methyl ester of 15a, 15b, and 15c was carried out under basic conditions, followed by an acidic work up, during which the pH was maintained above 4 to prevent trityl deprotection. After recrystallization for solid product or flash chromatography for oil products, 6-trityloxyhexanoic acid 16a, 9-trityloxynonanoic acid 16b and 12-trityloxydodecanoic acid 16c were isolated, providing aliphatic side-chains that were ready to be coupled to 12 and 13.