Dimethylformamide → HCID 68810693, compound

Temperature

0 °C

To a slurry solution of sodium hydride (60%, 0.13 g, 3.28 mmol) in N,N-dimethylformamide were added 4-{4-[(tert-butyl-dimethyl-silanyloxy)-methyl}-3-methoxy-phenyl}-but-3-ene-2-one (0.50 g, 1.54 mmol) and methyl benzoate (0.26 g, 1.97 mmol) at 0° C. The reaction was stirred at 0° C. for 1 h. The reaction mixture was removed from ice-bath and heated for 1 h at 60° C. The reaction was cooled to room temperature and quenched with aqueous 1.0 N hydrochloric acid (2.0 mL) slowly. Excess tetrabutylammonium fluoride was added to the above solution to deprotect the silyl group. The reaction was diluted with ethyl acetate (200 mL), washed with water (3×60 mL) and saturated aqueous sodium chloride (50 mL). The organic layer dried over magnesium sulfate, filtered, and concentrated to give impure crude product. Purification on silica (9:1 to 7:3 hexanes/ethyl acetate) to afford 5-(hydroxy-3-methoxy-phenyl)-1-phenyl-pent-4-ene-1,3-dione (0.14 g, 30% yield) as a solid: MS (EI) for C18H16O4: 297 (MH+).

1. customThe reaction mixture was removed from ice-bath
2. temperatureheated for 1 h at 60° C
3. temperatureThe reaction was cooled to room temperature
4. customquenched with aqueous 1.0 N hydrochloric acid (2.0 mL) slowly
5. additionExcess tetrabutylammonium fluoride was added to the above solution
6. additionThe reaction was diluted with ethyl acetate (200 mL)
7. washwashed with water (3×60 mL) and saturated aqueous sodium chloride (50 mL)
8. dry with materialThe organic layer dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customto give impure crude product
12. customPurification on silica (9:1 to 7:3 hexanes/ethyl acetate)

ORD record

ord-e375e992e67240d4ac724171ed640d11

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710038B2