Methyl iodide → 2-Methoxymethyl-3-methyl-thiophene

Participants

Reaction Steps

Sodium hydride (2.2 g ˜60%, 55.2 mmol, 1.2 equiv.) was suspended in dry tetrahydrofuran under an inert atmosphere. At 5° C. a solution of (3-methyl-thiophen-2-yl)-methanol (5.16 g, 46 mmol) in dry tetrahydrofuran was added dropwise. The mixture was stirred at room temp. for 1 hour, then iodomethane (7.8 g, 55.2 mmol, 1.2 equiv.) was added dropwise. The mixture was stirred overnight at room temp. and then quenched with diluted acid and extracted with diethyl ether. The combined organic extracts were washed with brine, dried over magnesiumsulfat dihydrate, filtered and evaporated to give 5.7 g of the title compound as a light green oil. GC-MS (EI) M=142.

Provenance & Evidence