3-Hydroxybenzyl alcohol → 3-[(6-Methyl-2-pyridinyl)oxy]benzenemethanol

HRID 1666388

Reaction equation

[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:17][C:13]1[N:12]=[C:11]([O:9][C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

3-Hydroxymethyl-phenol (3.69 g, 29.7 mmol), 2-fluoro-6-methyl-pyridine (3.00 g, 27 mmol,) and cesium carbonate (9.68 g, 29.7 mmol) were suspended in dimethylsulfoxide (25 mL) and heated to 110° C. After stirring for 16 h, the reaction was partitioned between water (250 mL) and ethyl acetate (250 mL). 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 (10-50%, EtOAc:heptane) to afford the title compound (3.72 g, 64% yield) as an off-white solid.

Workup

customthe reaction was partitioned between water (250 mL) and ethyl acetate (250 mL)
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 (10-50%, EtOAc:heptane)

Sources & evidence

ORD record: ord-9ea66b4dec644cb4a889b38fdfe4acff
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Linked notes

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