Methyl iodide → Methyl 2-(4-t-butylphenyl)propanoate

23.3 mL of lithium bis(trimethylsilyl)amide (1.0 M, 23 mmols) was added dropwise to 4.75 g (23 mmols) of methyl 4-tert-butylphenylacetate in 100 mL of dry THF at −78° C. while stirring under nitrogen. The mixture was stirred at this temperature for 45 minutes, then 1.5 mL (24 mmol) methyl iodide was added dropwise and the solution was stirred for an additional 1 hour at −78° C. The mixture was poured into 200 mL of H20 and the desired product was extracted with 500 mL diethyl ether. The organic layer was backwashed once with 500 mL H2O, dried over K2CO3, and concentrated under reduced pressure to yield 5.12 g of a dark oil. The oil was purified via silica gel chromatography eluting with a solvent gradient of hexane to hexane/ethyl acetate 19:1. The fractions containing the desired product were combined and concentrated under reduced pressure to yield the title compound 2.65 g (53%).

1. stirringThe mixture was stirred at this temperature for 45 minutes
2. stirringthe solution was stirred for an additional 1 hour at −78° C
3. additionThe mixture was poured into 200 mL of H20
4. extractionthe desired product was extracted with 500 mL diethyl ether
5. dry with materialdried over K2CO3
6. concentrationconcentrated under reduced pressure

ORD record

ord-572334f3748a4b30824c4745d6ad33cc

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06521605B1