Water → Dibenzyl ether

Participants

Reaction Conditions

Reaction Steps

A solution of 8a (0.440 g, 1.01 mmol) in dry dimethylformamide (1 mL) was added to a solution of sodium phenoxide (0.140 g, 1.20 mmol) and the mixture heated to 80° C. for three hours. The reaction mixture was cooled, poured into water, and extracted with ether. The ether extracts were washed sequentially with water and 20% NaCl, dried (Na2SO4), and concentrated. Flash chromatography gave a purified benzyl ether (0.210 g, mp 81°-82° C.) which was directly deprotected as described above for 10 to give 11a. 2,3-Dihydro-4-(3-phenoxypropyl)-5-benzofuranol (11b) can be produced from 8b in similar fashion. 11a: mp 114-115° C.; 11b: mp 107°-108° C.

Provenance & Evidence