tert-BUTYL CHLORIDE → Methyl 5-(tert-butyl)-3-methylthiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

AlCl3 (15.60 g, 117 mMol) was suspended in CH2Cl2 (18 mL) and the mixture was cooled to −78° C. A solution of 12.28 g (78 mMol) of 102a in CH2Cl2 (9 mL) was added dropwise over 5 min. The mixture was stirred for 5 min. A solution of 8.9 mL (82 mMol) 2-chloro-2-methylpropane in CH2Cl2 (9 mL) was then added over 45 min, and the resulting mixture was stirred at −78° C. for 1 h. The reaction mixture was gradually warmed to room temperature and stirred for 24 h. The reaction mixture was then poured onto ice and extracted with CH2Cl2. The organic layer was dried with Na2SO4, and concentrated to an oil, which was purified on silica eluting with a gradient of CH2Cl2 in Hexane (0 to 10%) to afford 9.94 g (60%) of 102b.

Provenance & Evidence