Potassium Carbonate → Benzenemethanol, 3-hydroxy-5-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-

HRID 1666436Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH2:5][OH:6].Cl[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:6][CH2:5][C:4]1[CH:7]=[C:8]([OH:10])[CH:9]=[C:2]([O:1][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3,5-Dihydroxybenzyl alcohol (5.0 g, 40 mmol), 2-chloro-5-trifluoromethyl-pyridine (7.13 g, 39.2 mmol) and potassium carbonate (6.16 g, 44.6 mmol) were suspended in dimethylformamide (100 mL) and heated to 100° C. After stirring for 16 h, the reaction was cooled to room temperature and partitioned between water (500 mL) and ethyl acetate. The organic layer was separated and the aqueous was extracted again with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (10-75%, EtOAc:heptane) to afford the title compound (2.32 g, 20% yield) as a thick oil.

Workup

temperaturethe reaction was cooled to room temperature
custompartitioned between water (500 mL) and ethyl acetate
customThe organic layer was separated
extractionthe aqueous was extracted again with ethyl acetate
dry with materialThe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (10-75%, EtOAc:heptane)

Sources & evidence

ORD record: ord-ad43d14e47404c0f88ed4fda95d99592
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

Loading…