Phosphoric Acid → 3-(6-Bromopyridin-2-yl)-2,3-dimethylbutan-2-ol
Reaction equation
C[Mg]I.C([O:6][CH2:7][CH3:8])C.[CH2:9](OCC)C.[Br:14][C:15]1[N:20]=[C:19]([C:21](C)([CH3:27])[C:22](OCC)=O)[CH:18]=[CH:17][CH:16]=1.P(=O)(O)(O)O>O>[Br:14][C:15]1[N:20]=[C:19]([C:21]([CH3:22])([CH3:27])[C:7]([CH3:8])([OH:6])[CH3:9])[CH:18]=[CH:17][CH:16]=1Participants
Procedure
In a nitrogen atmosphere, 13 mL of 2 M methylmagnesium iodide/diethyl ether solution was added to diethyl ether (20 mL) solution of 2.72 g of ethyl 2-(6-bromopyridin-2-yl)-2-methylpropionate with cooling in an ice bath. The reaction liquid was stirred at room temperature for 3 hours, and then water and aqueous 10% phosphoric acid solution were added thereto, extracted with diethyl ether, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and then dried with anhydrous magnesium sulfate. After concentrated under reduced pressure, the residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 8/1) to obtain 1.47 g of the entitled compound as a colorless oily substance.
Workup
- temperaturewith cooling in an ice bath
- customThe reaction liquid
- extractionextracted with diethyl ether
- washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
- dry with materialdried with anhydrous magnesium sulfate
- concentrationAfter concentrated under reduced pressure
- customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 8/1)
Sources & evidence
- ORD record
- ord-952bde54264048dcac01c7537bffbd88
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834019B2
Reaction notes
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