Tetrahydrofuran → HCID 66709635, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of furan (10.9 ml, 150 mmol) in dry tetrahydrofuran (200 ml) is added dropwise, under nitrogen, n-butyllithium (2.5 M solution in hexane, 50 ml, 125 mmol) at −78° C. When the addition is complete, the reaction is stirred for 30 minutes at −78° C. A solution of 4-benzyloxy-2,6-dimethylbenzaldehyde (23.0 g, 96 mmol) in dry tetrahydrofuran (100 ml) is added dropwise over 30 minutes. On completion of the addition, the reaction is allowed to warm to room temperature and stirring is continued for 2 hours. A solution of saturated aqueous ammonium chloride solution (300 ml) is added and the reaction mixture is extracted with dichloromethane (3×250 ml). The organic extract are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The product, ([4-benzyloxy-2,6-dimethylphenyl]furan-2-yl)methanol (32 g) is used without further purification in the next step.

Provenance & Evidence