Ethyl isobutyrate → Nonanoic acid, 9-bromo-2,2-dimethyl-, ethyl ester

Temperature

-78 °C

To a solution of diisopropylamine (5.82 mL) in THF (30 mL) was added n-butyllithium (2.5M in hexanes, 16.4 mL) at 0° C. and the mixture was stirred for 30 min at this temperature before being cooled to −78° C. Ethyl isobutyrate (5 mL) was added dropwise and the resultant mixture was stirred at −78° C. for 1 h before addition of 1,7-dibromoheptane (6.4 mL). The reaction mixture was stirred at −78° C. for 1 h then at RT for 2 h before being poured into saturated ammonium chloride solution. The solution was extracted with ethyl acetate (×2) then the combined organics were washed with brine, dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 0-10% ethyl acetate in cyclohexane to give the subtitled compound as a colourless liquid. Yield 1.27 g.

1. stirringThe reaction mixture was stirred at −78° C. for 1 h
2. extractionThe solution was extracted with ethyl acetate (×2)
3. washthe combined organics were washed with brine
4. dry with materialdried over sodium sulphate
5. filtrationfiltered
6. customevaporated in vacuo
7. customPurification
8. washeluting with 0-10% ethyl acetate in cyclohexane

ORD record

ord-6b0a3a1200b2484faf5a59927d0b6f59

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2