Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)- → HCID 59379235, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of dichlorophenylmethyl sulfoxide (5.94 g, 28.4 mmol; K. C. Tin & T. Dust, Tetra. Lett. 1970, 4643) in THF (100 mL) at −78° C. was added LDA (1.8 M in THF, 20.5 mL, 36.9 mmol). The reaction mixture was stirred at −78° C. for 15 min and then was added 3-(1,1,2,2-tetrafluoro-ethoxy)-benzaldehyde (6.94 g, 31.3 mmol). After stirring at −78° C. for 45 min, EtMgBr (1.0 M solution in t-BuOMe, 60 mL, 60 mmol) was added. The reaction mixture was stirred at −78° C. for another 40 min, quenched with NH4Cl aqueous solution and acidified with 1 N HCl. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic phases were dried (Na2SO4), concentrated and purified by column chromatography to give 4.13 g (49%) of A2a as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.89 (dd, J=7.6, 2.6 Hz, 1H), 7.81 (s, 1H), 7.58-7.46 (m, 2H), 5.95 (tt, J=53.0, 2.7 Hz, 1H), 4.68 (s, 2H); MS (ES) m/z: 293 (M+Na+).

Provenance & Evidence