Tetrabutylammonium Fluoride → 16-(Tetrahydro-2h-pyran-2-yloxy)hexadec-11-yn-1-ol

Tetra-n-butylammonium fluoride (3.14 g, 12.5 mL of a 1 M soln in THF, 12.50 mmol) was added to a solution of the above crude tert-butyldiphenyl-[16-(tetrahydropyran-2-yloxy)hexadec-11-ynyloxy]silane (6 g, 10.42 mmol) in THF (150 mL) under an argon atmosphere. After 5 h, the reaction mixture was quenched with sat. aq. NH4Cl (5 mL), washed with water (100 mL), and brine (75 mL). The aqueous layer was back-extracted with ether (2×75 mL). The combined organic extracts were dried over Na2SO4, concentrated under reduced pressure, and the residue was purified by SiO2 column chromatography using 5-10% EtOAc/hexanes as eluent to give 16-(tetrahydro-2H-pyran-2-yloxy)hexadec-11-yn-1-ol (3.17 g, 80% overall) as a colorless oil. TLC: 40% EtOAc/hexanes, Rf≈0.4; 1H NMR (CDCl3, 300 MHz) δ 4.57-4.59 (m, 1H), 3.82-3.90 (m, 1H), 3.71-3.79 (m, 1H), 3.64 (t, 2H, J=6.8 Hz), 3.46-3.53 (m, 1H), 3.36-3.44 (m, 1H), 2.10-2.22 (m, 4H), 1.20-1.80 (m, 26H).

1. customthe reaction mixture was quenched with sat. aq. NH4Cl (5 mL)
2. washwashed with water (100 mL), and brine (75 mL)
3. extractionThe aqueous layer was back-extracted with ether (2×75 mL)
4. dry with materialThe combined organic extracts were dried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customthe residue was purified by SiO2 column chromatography

ORD record

ord-dcde4bb652594ada8d19be4f2a0fc965

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272991B2