Reaction SMILES: C(O)C.Cl.CO.[CH3:7][C@:8]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][O:9]1>C(OCC)(=O)C>[CH3:7][C:8]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][O:9]1
Reactant: C[C@]1(C(=O)O)CCCO1
Agent: Cl
Solvent: CCOC(C)=O
Solvent: CO
Solvent: CCO
Product: CC1(C(=O)O)CCCO1

Procedure:
The major batch obtained above (88 g) was dissolved in 240 mL hot (60-65° C.) ethanol and cooled to room temperature gradually. After 24 h, no crystals had formed. Crystallization was induced by gradual and careful cooling to 8° C. when fine needles began to form. This mixture, after filtration over sintered glass and washing with cold acetone (−60° C.), provided 10 g of a free-flowing salt. The filtrate obtained was put on the rotovap until crystal began to form in the flask. It was then allowed to crystallize at 6° C. This provided 3 g more of the salt. The filtrate was again placed on the rotovap but more ethanol was removed (so that more crystals were formed in the flask) before recrystallizing the mixture at 4-5° C. This was repeated and together obtained 30 g more of the salt after filtration and washing as described above. A total of 43 g of salt was obtained from the first recrystallization. This material was dissolved in 120 mL of hot ethanol and left standing at for 48 hr at room temperature. This provided very few needles. The flask was cooled slowly to 4° C. to induce more recrystallization. This mixture containing fine needles was filtered over sintered glass and washed with cold acetone (−60° C.). More needles formed in the filtrate after addition of the acetone. This was also collected over sintered glass and washed with cold acetone. The process was repeated until no more solid came out from the filtrate. The clear filtrate was put on the rotovap and solvents were removed until cloudiness formed in the flask. This was then cooled to 4° C. to coax out more crystals which was collected as described before. This process of crystallization was repeated until crystallization ceased. A total of 33 g of material was obtained from the second crystallization. This material was subjected to 85 mL of hot ethanol and recrystallized again. This time, a substantial amount of needles came out above room temperature. This was collected and the filtrate treated as described before for the previous recrystallizations to provide 29.8 g of a free-flowing material after the third recrystallization. This white powder was dissolved in 78 mL of hot ethanol for the fourth recrystallization. This time, needles came out at room temperature. The fine needles (15 g) were harvested and the filtrate treated as previously described, to provide a total of 27.6 g of a white powder after pumping. The needles were crushed before pumping as they had a tendency to impregnate ethanol. 40 mg of this material was treated with 0.5 mL of a 3.85 M ethyl acetate solution of hydrogen chloride (g) to liberate the acid. The amine salt was removed by trituration with ether followed by filtration over sintered glass. The acid thus obtained had the following optical activity: [α]20D=−9.49 (c=0.78, MeOH), [α]20578=−10.38 (c=0.78, MeOH). For use in subsequent reactions, the 2(R)-methyl tetrahydrofuran-2-carboxylic acid was liberated from the salt using a solution of hydrogen chloride(g) in ethyl acetate.