Water → HCID 58520617, compound

HRID 511819Notes

Reaction equation

HRID 511819 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][CH:17]1[CH2:19][CH2:18]1.O>CN(C=O)C>[CH:17]1([CH2:16][O:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 142752-Methyl-5-hydroxypyridineHCID 81503Bromomethylcyclopropane

Product 1

HCID 58520617HCID 58520617, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methylpyridin-3-ol (5.0 g, 46 mmol) in DMF (45 mL) were added cesium carbonate (16.5 g, 53 mmol) and (bromomethyl)cyclopropane (7.1 g, 53 mmol) at room temperature. After being stirred at room temperature for 18 hours, the mixture was poured into H2O, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1 (v/v)) to give 3.9 g (52% yield) of the title compound as a yellow oil:

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1 (v/v))

Sources & evidence

ORD record
ord-643c4c32de0c4749881b1d0b8f1a1bc6
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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