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In a 500 mL 3-necked round bottom flask fitted with a Claisen head with N2 inlet, a West condenser, a thermocouple-J-KEM controller and an addition funnel was added a solution of tert-butylmagnesium chloride (341 mL of a 1.0 M solution, 341 mmole, 3 equiv.) at about 60° C. Methyl-(R)-3-(2′-bromo-1′-oxooctyloxy)tetradecanoate (52.6.0 g, 113.5 mmole, 1 equiv.) (“bromodiester”) and 25 mL of dry THE were added to an addition funnel. The bromodiester mixture was slowly added to the t-BuMgCl/THF mixture at reflux over about one hour. The reaction mixture was sampled at 1 and 2 hours at about 60° C. (resulting in 90 and 91% area normalized gas chromatography (AN GC) analysis, respectively). After 2 hours the resulting reaction mixture was cooled and concentrated on a roto-evaporator to about ⅓ to about ½ the original volume. The resulting syrupy mixture was taken up in about 250 mL of toluene (or an ether, such as methyl tert-butyl ether and the like; a hydrocarbon, such as hexane, heptane, and the like; or mixtures thereof) and added to a mixture containing 250 mL of toluene, 75 mL of 10% HCl in a 1 L jacketed flask keeping the quenched solution below 30° C. The aqueous layer was removed. The organic layer washed one time with 50 mL of 1.0 N HCl solution. The aqueous layer was removed, the organic layer washed one time with 50 mL of water, dried over magnesium sulfate, filtered and concentrated. This resulted in a gel-like solid residue. The residue was dissolved in 250 mL of ethyl acetate at 40° C. The ethyl acetate was removed on the roto-evaporator. The resulting crude off-white solid (42.4 g) was slurried up in about 100 mL of hexane and cooled to 0° C., filtered and rinsed with 50 mL of cold hexane followed by another 25 mL of cold hexane. The isolated white solids were air dried under vacuum for about 1 to 2 hours resulting in 31.4 g of (6R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-pyran-2-one (78.4% yield).

1. customIn a 500 mL 3-necked round bottom flask fitted with a Claisen head with N2 inlet
2. additionwere added to an addition funnel
3. temperatureat reflux over about one hour
4. aliquotThe reaction mixture was sampled at 1 and 2 hours at about 60° C. (
5. customresulting in 90 and 91% area
6. customAfter 2 hours the resulting reaction mixture
7. temperaturewas cooled
8. concentrationconcentrated on a roto-evaporator to about ⅓
9. additionor mixtures thereof) and added to a mixture
10. additioncontaining 250 mL of toluene, 75 mL of 10% HCl in a 1 L
11. customthe quenched solution below 30° C
12. customThe aqueous layer was removed
13. washThe organic layer washed one time with 50 mL of 1.0 N HCl solution
14. customThe aqueous layer was removed
15. washthe organic layer washed one time with 50 mL of water
16. dry with materialdried over magnesium sulfate
17. filtrationfiltered
18. concentrationconcentrated
19. customThis resulted in a gel-like solid residue
20. customThe ethyl acetate was removed on the roto-evaporator
21. filtrationfiltered
22. washrinsed with 50 mL of cold hexane
23. customdried under vacuum for about 1 to 2 hours