Dimethylformamide → HCID 57989086, compound

tert-Butyl(3-(2-fluorophenyl)propoxy)dimethylsilane (example 88, step b) (4.4 g) was added dropwise over 5 min to a solution of sec-butyllithium (1.4M in cyclohexane, 11.7 mL) and 1,1,4,7,7-pentamethyldiethylenetriamine (3.4 mL) in THF (25 mL) at −78° C. The resulting mixture was stirred for 2 h, then DMF (6.4 mL) was cautiously added and the resulting mixture allowed to warm to RT and stirred overnight. The reaction was quenched with water (100 mL) and then ethyl acetate (250 mL) was added. The phases were separated and the organic phase washed with water (2×100 mL), 2M HCl solution (2×50 mL), and brine (100 mL), then dried over magnesium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with isohexane to 10% ether in isohexane gradient. The product containing fractions were combined and evaporated to give the subtitled compound as a clear oil. Yield 1 g.

1. stirringstirred overnight
2. customThe reaction was quenched with water (100 mL)
3. additionethyl acetate (250 mL) was added
4. customThe phases were separated
5. washthe organic phase washed with water (2×100 mL), 2M HCl solution (2×50 mL), and brine (100 mL)
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. customevaporated
9. customPurification
10. washeluting with isohexane to 10% ether in isohexane gradient
11. additionThe product containing fractions
12. customevaporated

ORD record

ord-465cd3c84ee6460aaa53c945280033fc

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2