Water → HCID 55267997, compound

Ethyl 3-(4-fluoro-3-methoxyphenyl)propanoate (1.019 g, 4.50 mmol) was dissolved in THF (22.52 ml) under nitrogen. A solution of lithium aluminum hydride (4.50 ml, 9.01 mmol) was added slowly. TLC shows reaction done after about 10 min. Water (0.35 mL) was slowed added and then the mixture was stirred for 30 min. 1 N NaOH (1.05 mL) was added and the reaction was stirred for 30 min. Additional water was added (0.35 mL) and the solution was stirred and then filtered. The cake was washed with ether and then rotovapped. Ether was added. The solution was dried over magnesium sulfate and then filtered and rotovapped. The solution was passed through silica gel with methylene chloride then ethyl acetate then rotovapped to give 3-(4-fluoro-3-methoxyphenyl)propan-1-ol (0.753 g, 4.09 mmol, 91% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3). δ ppm 6.98 (dd, 1H), 6.80 (dd, 1H), 6.71 (ddd, 1H), 3.89 (s, 3H), 3.68 (t, 2H), 2.68 (t, 2H), 1.94-1.82 (m, 2H), 1.33 (s, 1H)

1. customreaction
2. stirringthe reaction was stirred for 30 min
3. stirringthe solution was stirred
4. filtrationfiltered
5. washThe cake was washed with ether
6. additionEther was added
7. dry with materialThe solution was dried over magnesium sulfate
8. filtrationfiltered

ORD record

ord-e9b1fdf073754fbab4f7c08378c9c1fc

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217027B2