Water → HCID 20109584, compound

Participants

Reaction Steps

A solution of 1-(4-(2-methoxyethoxy)phenyl)propan-1-one oxime (1.5 g, 6.7 mmol) in tetrahydrofuran (20 mL) was added dropwise to a stirred suspension of lithium aluminum hydride (0.78 g, 20.55 mmol) in tetrahydrofuran (48 mL) at room temperature under nitrogen. After 18 hours the mixture was heated at reflux for 3 hours, then allowed to cool. 0.8 mL of water was added drop-wise, followed by 0.8 mL of 15% aq sodium hydroxide, and then 2.4 mL of water. After several minutes the mixture was filtered, and the residue washed twice with tetrahydrofuran. The combined filtrate and washings were concentrated in vacuo, leaving 1.34 g of clear golden oil, which was flash chromatographed on a column (5×10 cm) of silica gel eluting with Hxa/EtOAc/acetone 8:1:1 to afford 0.83 g of the product as a clear golden oil; mass spec ES+m/z=210 (m+1).

Provenance & Evidence