Tetrabutylammonium Fluoride → (E)-methyl 4-(3,3,3-trifluoroprop-1-enyl)-2-methoxybenzoate

MS 4 Å (powder, 16 g) was added to a 1 M solution of TBAF in THF (20 mL, 20 mmol), and the mixture was stirred at room-temperature overnight under an argon atmosphere. To the mixture were added a solution of methyl 4-formyl-2-methoxybenzoate (420 mg, 0.0022 mol) and 2,2,2-trifluoroethyldiphenylphosphine oxide (1.23 g, 0.00432 mol) in THF (20 mL). After the mixture was stirred for 2 h, MS 4 Å was removed by filtration. The filtrate was concentrated and water (120 mL) was added. The mixture was extracted with AcOEt. The extract was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by column chromatography on silica gel using AcOEt-hexane (0-15%) as eluent to give (E)-methyl 4-(3,3,3-trifluoroprop-1-enyl)-2-methoxybenzoate as a white solid, followed by (Z)-methyl 4-(3,3,3-trifluoroprop-1-enyl)-2-methoxybenzoate as a colorless oil.

1. stirringAfter the mixture was stirred for 2 h
2. customMS 4 Å was removed by filtration
3. concentrationThe filtrate was concentrated
4. additionwater (120 mL) was added
5. extractionThe mixture was extracted with AcOEt
6. washThe extract was washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customThe residue was purified by column chromatography on silica gel

ORD record

ord-fcddb2ce6a4846f08d649ce672a01d31

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576099B2