Dimethylformamide → 6-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A cooled (−20° C.) mixture of 6-methoxy-2,3-dihydrobenzo[b][1,4]dioxine (2.119 g; 12.80 mmol), and N1,N1,N2,N2-tetramethylethane-1,2-diamine (2.28 ml; 15.30 mmol) in anh. THF (100 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (8.00 ml; 12.80 mmol). The resulting mixture was further stirred at −20° C. for 1 h. Anh. DMF (5.0 ml; 64.57 mmol) was then added, and the mixture was stirred at rt for 20 min. Aq. sat. NH4Cl and Et2O were successively added, and the aq. layer was further extracted with Et2O. The mixed organic layers were washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=1/1) afforded 6-methoxy-2,3-dihydrobenzo[b][1,4]dioxine-5-carbaldehyde as a yellow oil. LC-MS (conditions A): tR=0.52 min.; [M+H]+: 195.19 g/mol.

Provenance & Evidence