Veratraldehyde → HCID 69662836, compound

A solution of 3,4-dimethoxybenzaldehyde (1.06 g, 6.4 mmol), (S)-1-methyl-2-phenylethylamine sulfate (1.18 g, 6.4 mmol) and triethylamine (0.89 ml, 6.4 mmol) in 1,2-dichloroethane (50 ml) was stirred at room temperature under argon for 15 min. Sodium triacetoxyborohydride (2.97 g, 14 mmol) was added over 5 min. then stirring was continued for a further 16 h. The reaction mixture was diluted with MDC (50 ml) then washed with saturated aqueous K2CO3. The aqueous phase was extracted with MDC and the combined organics washed with brine. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was chromatographed (silica gel, 0–100% EtOAc-pentane) to afford the title compound as a colourless oil (1.20 g, 67%).

1. additionThe reaction mixture was diluted with MDC (50 ml)
2. washthen washed with saturated aqueous K2CO3
3. extractionThe aqueous phase was extracted with MDC
4. washthe combined organics washed with brine
5. dry with materialThe organic phase was dried (MgSO4)
6. customthe solvent removed in vacuo
7. customThe residue was chromatographed (silica gel, 0–100% EtOAc-pentane)

ORD record

ord-271befcf31bf4de5be010ffc3ee4aa19

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07078565B2