Trifluoroacetic acid → HCID 18765814, compound

Participants

Reaction Steps

A mixture of 20 mL of CH2Cl2, 20 mL H2O, 415 mg (1 eq) of tetramethylhydroquinone (D), 200 mg of NaOH, 540 mg (1.1 eq) of t-butylbromoacetate, 760 mg of C were stirred at room temperature, under argon, for 12 hr. Initially, D was not completely soluble, but with time, in 1 hr, it completely dissolved. After 12 hr, acid was added to bring the pH to 7.0, 200 mL of CH2Cl2 was added, and the reaction mixture was extracted with brine (4×200 mL), dried over Na2SO4, and evaporated under reduced pressure to yield crude product. 5 mL of TFA was added to the crude product, and the mixture was stirred for 1 hr. TFA was evaporated and the crude product charged on silica gel (230-400 mesh, CH2Cl2 -EtOAc, 2:1) to yield 270 mg (49%) of product 27.

Provenance & Evidence