Sodium Hydroxide → 2-(4-Fluorophenyl)-2-methylpropan-1-ol

Temperature

0 °C

Methyl 2-(4-fluorophenyl)-2-methylpropanoate (5.08 g, 26.9 mmol) was dissolved in THF (51 ml) and cooled to 0° C. before adding a solution of lithium aluminium hydride (1M in THF) (38.8 ml, 38.8 mmol) dropwise over 30 mins. When the addition was complete, the reaction was warmed to r.t. and stirred for 3 h. After recooling on ice, water (1.35 ml) was added cautiously followed by 15% NaOH in water (1.35 ml) and more water (4.05 ml). The suspension was stirred at r.t. for 30 mins before the solid was filtered off and washed with THF (2×30 ml). The solvent was evaporated and the product purified by chromatography with EtOAc/heptanes to give a clear oil (3.48 g, 80%): MS (ESI+) for C10H13FO m/z 168.2 [M+H]+; LC purity 94% (ret. time, 1.76 min); 1H NMR (500 MHz, CDCl3) δH 7.41-7.32 (m, 2H), 7.15-7.00 (m, 2H), 3.62 (d, J=6.4 Hz, 2H), 1.35 (s, 6H).

1. additionWhen the addition
2. temperaturethe reaction was warmed to r.t.
3. additionwas added cautiously
4. stirringThe suspension was stirred at r.t. for 30 mins before the solid
5. filtrationwas filtered off
6. washwashed with THF (2×30 ml)
7. customThe solvent was evaporated
8. customthe product purified by chromatography with EtOAc/heptanes

ORD record

ord-003728a2696c4a579afba0a50511a67b

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580762B2