Triphenylphosphine → Ethyl 3-(2,6-dimethylbenzyloxy)phenylacetate

Participants

Reaction Steps

A solution of 2,6-Dimethylbenzyl alcohol (5.25 g, 38.6 mmol) and diisopropyl azodicarboxylate (DIAD, 8.49 g, 42 mmol) in THF (30 ml) and DMF (13 ml) was added drop wise to a solution of Ethyl 2-(3-hydroxyphenyl)acetate (Step A, 6.66 g, 37 mmol) and triphenylphosphine (TPP, 11 g, 42 mmol) in THF (100 ml). The reaction mixture was stirred at room temperature for 4 hours, diluted with ether and washed with water. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate, 4:1) to give the title compound.

Provenance & Evidence