Acetic Acid → 3-Decanone, 1-(4-hydroxy-3-methoxyphenyl)-5-methoxy-

A solution of [6]-shogaol (100 mg, 0.36 mmol) in methanol (5 mL) at 0° C. was treated with a solution of sodium (21 mg, 0.91 mmol) in methanol (1 mL). After 4.0 h, glacial acetic acid (0.5 mL) was added, and the solution was concentrated under reduced pressure. The residue was dissolved in water (5 mL), and extracted with ethyl acetate (5 mL×3). The organic phases were pooled, washed with water (5 mL×2) and brine (5 mL×1), dried over Na2SO4, and evaporated in vacuo. The residue was subjected to preparative TLC (hexane/EtOAc=4:1) to give the title compound M7 as a yellow oil (100 mg, yield 90%); 1H NMR (600 MHz, CDCl3) δ 6.69 (1H, d, J=1.6 Hz, H-2′), 6.82 (1H, d, J=8.1 Hz, H-5′), 6.66 (1H, dd, J=8.1, 1.6 Hz, H-6′), 2.75 (2H, m, H-1), 2.83 (2H, t, J=7.5 Hz, H-2), 2.64 (1H, dd, J=15.7, 7.6 Hz, H-4a), 2.40 (1H, dd, J=15.7, 4.7 Hz, H-4b), 3.66 (1H, m, H-5), 1.48 (1H, m, H-6a), 1.42 (1H, m, H-6b), 1.31-1.25 (6H, m, ranged from H-7 to H-9), 0.88 (3H, t, J=7.1 Hz, H-10), and 3.87 (3H, s, OMe-3′); positive APCIMS, m/z 309 [M+H]+.

1. concentrationthe solution was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in water (5 mL)
3. extractionextracted with ethyl acetate (5 mL×3)
4. washwashed with water (5 mL×2) and brine (5 mL×1)
5. dry with materialdried over Na2SO4
6. customevaporated in vacuo

ORD record

ord-ba91febbb721428a9790a5f7a75e6e85

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272994B1