1-Bromopropane → HCID 67267937, compound

HRID 598116Notes

Reaction equation

HRID 598116 reaction equation
[C:1]1([CH3:17])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][CH:10]=1.[H-].[Na+].Br[CH2:21][CH2:22][CH3:23]>CN(C)C=O>[C:1]1([CH3:17])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:14]=[C:13]([CH2:15][O:16][CH2:21][CH2:22][CH3:23])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 67267450HCID 67267450, compound

Product 1

HCID 67267937HCID 67267937, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(6-Mesitylpyridin-2-yl)methanol (1.03 g, 4.54 mmol) was dissolved in N,N-dimethylformamide (5 mL) and the solution was charged with sodium hydride (60% dispersion in mineral oil, 0.23 g, 5.7 mmol). The reaction stirred for 0.5 h at room temperature. Bromopropane (0.52 mL, 5.7 mmol) was added last. The reaction ran for 2.5 h. The solution was quenched with water, extracted with ether, dried, and concentrated. Flash chromatography (15% ethyl acetate/hexanes) gave 0.65 g (53% yield) of the desired product.

Workup

  1. waitThe reaction ran for 2.5 h
  2. customThe solution was quenched with water
  3. extractionextracted with ether
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d984e0702252461390c32b2974a186f3
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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