Acetone → 4-(6-Bromopyridin-2-yl)-2-methylbut-3-yn-2-ol

HRID 386033

Reaction equation

C([Li])CCC.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[CH:14])[N:8]=1.[CH3:15][C:16]([CH3:18])=[O:17]>O1CCCC1>[Br:6][C:7]1[N:8]=[C:9]([C:13]#[C:14][C:16]([CH3:18])([OH:17])[CH3:15])[CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (0.6 mL of 1.6M in hexanes, 0.96 mmol) was added to a cooled (−78° C.) solution of 2-bromo-6-ethynylpyridine (150 mg, 0.82 mmol) in tetrahydrofuran (4.1 mL). A tan slurry formed. The mixture was stirred for 30 minutes while warming to −30° C. at which time acetone (0.3 mL, 4.1 mmol) was added. The slurry dissolved to form a light orange solution. The reaction was stirred for an additional 2 hours while warming to 0° C. The reaction was quenched via the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered, concentrated in vacuo and purified via flash chromatography (0-50% ethyl acetate/hexanes) to afford the title compound as a white solid.

Workup

customA tan slurry formed
additionwas added
dissolutionThe slurry dissolved
customto form a light orange solution
stirringThe reaction was stirred for an additional 2 hours
customThe reaction was quenched via the addition of saturated aqueous ammonium chloride
extractionextracted with ethyl acetate (2×)
dry with materialThe combined organics were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified via flash chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-4928e682b0a34119ad5229caccc23a87
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Linked notes

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