Sodium hydride → Methyl 2-[(4-bromophenyl)(pyridin-2-yl)methoxy]-4-methylpentanoate

HRID 1180391Notes

Reaction equation

HRID 1180391 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[OH:9])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:19]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:20]([O:22][CH3:23])=[O:21]>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[O:9][CH:19]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 12177878(4-Bromophenyl)(pyridin-2-yl)methanolHCID 12957039Methyl 2-bromo-4-methylpentanoate

Product 1

HCID 69473468Methyl 2-[(4-bromophenyl)(pyridin-2-yl)methoxy]-4-methylpentanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (4-bromophenyl)(pyridin-2-yl)methanol from step 1 (720 mg, 2.73 mmol) in DMF (14 mL) at 0° C., was added sodium hydride portionwise (69 mg, 2.87 mmol). The mixture was stirred 30 minutes before the methyl 2-bromo-4-methylpentanoate was slowly added (469 μL, 2.87 mmol). The reaction was allowed to warm to room temperature and was aged for 3 hours more. The mixture was then poured into brine and extracted 3 times with ethyl acetate. The combined organic extracts were dried and concentrated and the crude product obtained was chromatographed on silica gel using 50% ethyl acetate in hexanes to afford the title compound.

Workup

  1. additionwas slowly added (469 μL, 2.87 mmol)
  2. extractionextracted 3 times with ethyl acetate
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customthe crude product obtained
  6. customwas chromatographed on silica gel using 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5af5cccedb664e0482317b38c752fc4f
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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