Phenylacetylene → 1-(2,6-Dimethoxy-pyridin-3-yl)-3-phenyl-prop-2-yn-1-ol

HRID 1037241Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH3:14][O:15][C:16]1[C:21]([CH:22]=[O:23])=[CH:20][CH:19]=[C:18]([O:24][CH3:25])[N:17]=1.[Cl-].[NH4+]>C1COCC1>[CH3:14][O:15][C:16]1[C:21]([CH:22]([OH:23])[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:20][CH:19]=[C:18]([O:24][CH3:25])[N:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of phenylacetylene (0.61 g, 5.98 mmol) in dry THF (10 mL), cooled to −78° C., was added 2.5 M nBuLi in hexanes (2.4 mL, 6.0 mmol). The mixture was stirred for 15 min at −78° C., followed by addition of a solution of 2,6-dimethoxypyridine-3-carbaldehyde (1.0 g, 6.0 mmol) in THF (10 mL) was added over 5 minutes. The reaction mixture was allowed to warm to 0° C. and saturated ammonium chloride was added. The resultant biphasic mixture was separated and extracted twice with ethyl acetate. The combined organic phase was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 10 to 30% ethyl acetate in cyclohexane) to afford the title compound (1.60 g, 99%) as a colourless gum. LCMS (Method B): RT=4.38 min, [M+H]+=270.

Workup

additionwas added over 5 minutes
temperatureto warm to 0° C.
customThe resultant biphasic mixture was separated
extractionextracted twice with ethyl acetate
washThe combined organic phase was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-cc111004737041c79f218cf108a9f62b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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