(R)-4-chlorohept-6-yn-1-ol synthesis

Yield:1583253-09-1 97%

Reaction Conditions:

with pyridine;pyridine hydrofluoride in acetonitrile at 0 - 20; for 10 h;

Steps:

S-6

[00266] To a stirred solution of TBDPS-ether S-2¹⁸ (3.10 g, 8.05 mmol, >99% ee) and pyridine (3.25 mL, 40.3 mmol) in MeCN (40 mL) was added HF-pyridine complex (70% HF content, 1.46 mL, 56.4 mmol) at 0 °C.¹⁹ After stirring for 10 h at room temperature, the reaction mixture was carefully quenched with sat. NaHC0₃ aq and solid NaHC0₃ at 0 °C. The aqueous phase was extracted with EtOAc three times and the combined organic phases were washed with 1 M HCl aq and brine, dried over Na₂S0₄, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluent: 10% then 40% EtOAc in hexanes) to give alcohol S-3 (1.13 g, 97%) as a colorless oil.

References:

WO2016/3975,2016,A1 Location in patent:Paragraph 00266