Dimethylformamide → 3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde

Temperature

-78 °C

tert-Butyl(2-fluorophenethoxy)dimethylsilane (example 78, step a) (5.00 g) was added over 5 minutes to a stirred solution of sec-butyllithium (1.4 molar solution in cyclohexane, 14.0 mL) and N1-(2-(dimethylamino)ethyl)-N1,N2,N2-trimethylethane-1,2-diamine (4.10 mL) in THF (25 mL) cooled to −78° C. After 2 h, N,N-dimethylformamide (10.06 g) was added, the reaction mixture was stirred at −78° C. for 1 h, and then the cooling bath was removed. After a further 0.5 h, the reaction was quenched with water. Ethyl acetate (300 mL) was added and the reaction mixture washed with water (3×150 mL), 2M HCl (2×50 mL), water (2×50 mL), brine then dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as an oil. Yield 5.3 g.

1. customthe cooling bath was removed
2. waitAfter a further 0.5 h
3. customthe reaction was quenched with water
4. additionEthyl acetate (300 mL) was added
5. washthe reaction mixture washed with water (3×150 mL), 2M HCl (2×50 mL), water (2×50 mL), brine
6. dry with materialthen dried over sodium sulphate
7. filtrationfiltered
8. customevaporated in vacuo

ORD record

ord-e3b7cb78208e441492fc35e6b4e5c1aa

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2