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

HRID 511679Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9](OC)=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:13])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-08db30a9c5334a72bd7987170b0786f2
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096634B2

Reaction notes

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