Hydrochloric Acid → (E)-(2R,3R,4S,5S)-3,5-Dimethoxy-2,4-dimethyl-nona-6,8-dienoic acid

To (E)-(2R,3R,4S,5S)-3,5-Dimethoxy-2,4-dimethyl-nona-6,8-dienal (1.2 g, 5.3 mmol) in tert-butanol (24 ml) and 2-methyl-2-butene (5.6 ml, 53.1 mmol) at room temperature, was added a solution of sodium chlorite (2.4 g, 26.5 mmol) and sodium dihydrogenphosphate (1.5 g, 10.6 mmol) in water (5 ml). The reaction was stirred vigorously for 1.5 hours, after which brine (10 ml) was added and the reaction acidified to pH5 with 2M hydrochloric acid. The reaction was extracted with dichloromethane (3×), the organics dried through a hydrophobic frit and concentrated in vacuo. The oily residue was left on a vacuum pump overnight to afford the product 3c as an orange solid (1.02 g, 79%). 1H NMR (300 MHz, CDCl3) δ 6.39 (dt, J=16.7 Hz, 10.3 Hz, 10.0 Hz, 1H), 6.23 (dd, J=14.9 Hz, 10.5 Hz, 1H), 5.45 (dd, J=14.9 Hz, 8.7 Hz, 1H), 5.26 (d, J=16.3 Hz, 1H), 5.14 (d, J=10.3 Hz, 1H), 3.91 (dd, J=9.4 Hz, 1.8 Hz, 1H), 3.46 (s, 3H), 3.43 (m, 1H), 3.26 (s, 3H), 2.67 (m, 1H), 1.71 (m, 1H), 1.13 (d, J=7.1 Hz, 3H), 0.78 (d, J=7.1 Hz, 3H).

1. extractionThe reaction was extracted with dichloromethane (3×)
2. customthe organics dried through a hydrophobic frit
3. concentrationconcentrated in vacuo
4. waitThe oily residue was left on a vacuum pump overnight

ORD record

ord-8cbe9555a53e4ef0a3257a0214aa0e70

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513184B2