Hydrochloric Acid → HCID 86722513, compound

Ethyl 2-fluorohexadec-2-enoate mixture 50 (6.83 g, 16.6 mmol, purity: 73% (GC)) was dissolved in dry THF (23 mL). At 0° C. DIBAL-H (1 M solution in heptane, 56.8 mL, 56.8 mmol, 3.4 eq.) was added dropwise. The reaction mixture was allowed to warm up to r.t. overnight and was poured into water (50 mL). 2 M hydrochloric acid (50 mL) was added and the phases were separated. The aqueous layer was extracted with diethyl ether (3×50 mL) and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 10:1→5.1). The diastereomeric mixture was isolated as a waxy, white solid. Yield: 2.67 g (61%), purity: 98% (GC).

1. customAt 0° C
2. customthe phases were separated
3. extractionThe aqueous layer was extracted with diethyl ether (3×50 mL)
4. dry with materialthe combined organic layers were dried over Na2SO4
5. customThe solvent was removed under reduced pressure
6. customthe residue was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 10:1→5.1)
7. customThe diastereomeric mixture was isolated as a waxy, white solid

ORD record

ord-cc363a5db2a2490e995329bfab418ada

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345791B2