Tetrabutylammonium Fluoride → 3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol

TBAF (1.0 M in THF, 0.5 mL, 0.50 mmol, 1.2 equiv) was added in one portion to a dry THF (100 μL) solution of 3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine (0.2 g, 0.42 mmol, 1.0 equiv) and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated and the residue was partitioned between EtOAc (15 mL) and aqueous saturated ammonium chloride solution (10 mL). The layers were separated and the aqueous layer was extracted with 2 additional portions of EtOAc (10 mL). The combined extracts were dried (MgSO4), filtered, and concentrated to give crude 3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol, a thick, beige oil, which was used without further purification.

1. concentrationThe mixture was concentrated
2. customthe residue was partitioned between EtOAc (15 mL) and aqueous saturated ammonium chloride solution (10 mL)
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with 2 additional portions of EtOAc (10 mL)
5. dry with materialThe combined extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-da05a8846dc345258f92d7720204ce9a

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08545877B2