Methanol → HCID 59994483, compound

Participants

Reaction Steps

To lithium borohydride (2M in THF; 2.00 ml; 4.00 mmol) was added dropwise over 0.5 min chlorotrimethylsilane (1.02 ml; 8.00 mmol). A precipitate was formed and after ca. 3 min, 2-methyl-1-(methyloxy)-3-[(E)-2-nitroethenyl]benzene (Preparation 9, 193 mg; 1.00 mmol) in THF (4 ml) was added dropwise via syringe over 5 min, making sure that the temperature remained at ca. 25° C. (using a water cold bath). The solution was stirred at room temperature overnight. The mixture was cooled with an ice bath, methanol was added slowly, and the solvent removed. The residue was partitioned between 25% aqueous sodium hydroxide and dichloromethane (3 extractions), and the solvent evaporated. Purification of the residue by solid phase extraction (SCX column) gave the title compound (80 mg).

Provenance & Evidence