Acetone → HCID 21841981, compound

Temperature

-78 °C

To a solution containing 6 g of the title compound of Step C dissolved in 120 mL of dichloromethane and cooled to -78° C. under a nitrogen atmosphere was added 68.4 mL of 1.0 M of diisobutylaluminum hydride. The reaction was stirred at -78° C. for 1 h, then was allowed to warm to room temperature and was stirred overnight. The reaction was then cooled to -78° C. and 10 mL of acetone was added dropwise. To this mixture at -78° C. was added 10 mL of 1N sodium hydroxide dropwise. The reaction mixture was allowed to warm to room temperature and was then poured into water, and the resulting mixture was extracted with dichloromethane. The organic extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The filtrate was then evaporated to obtain 4.15 g of the title compound of Step D as a white solid melting at 117°-127° C. 1H NMR (400 MHz, CDCl3): δ 3.472 (s,3H), 3.969 (m,4H), 4.4-4.56 (m,2H), 7.19 (d,1H), 7.423 (t,1H), 7.485 (t,1H), 7.547 (d,1H).

1. temperatureto warm to room temperature
2. stirringwas stirred overnight
3. temperatureThe reaction was then cooled to -78° C.
4. temperatureto warm to room temperature
5. extractionthe resulting mixture was extracted with dichloromethane
6. washThe organic extracts were washed with saturated aqueous sodium chloride
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. customThe filtrate was then evaporated

ORD record

ord-01fd60d88e74458090b64471cad085ac

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05962436