1,4-Dioxane → HCID 90418490, compound

HRID 1484808Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:13]1[C:18]([CH2:19][OH:20])=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)(O)[O-].[Na+].O1CCOCC1>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[C:18]([CH2:19][OH:20])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 50-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (4-methoxyphenyl)boronic acid (1.6 g, 10.53 mmol, 1.20 equiv), (2-chloropyridin-3-yl)methanol (1 g, 6.97 mmol, 1.00 equiv), sodium bicarbonate (1.7 g, 20.24 mmol, 3.00 equiv), Pd(dppf)Cl2 (0.57 g, 0.10 equiv) in a solvent mixture of dioxane (10 mL) and water (10 mL). The resulting solution was stirred for 1.5 h at 100° C., and then it was diluted with 20 mL of H2O. The resulting solution was extracted with 2×50 mL of ethyl acetate, and the combined organic layers were concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:50-1:1) as eluent to furnish 1 g (67%) of [2-(4-methoxyphenyl)pyridin-3-yl]methanol as a colorless oil.

Workup

customInto a 50-mL round-bottom flask, which was purged
temperaturemaintained with an inert atmosphere of nitrogen
extractionThe resulting solution was extracted with 2×50 mL of ethyl acetate
concentrationthe combined organic layers were concentrated under vacuum

Sources & evidence

ORD record: ord-18efd585179749efb538b1f95619cf16
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422279B2

Reaction notes

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