Butyl bromide → HCID 19008984, compound

HRID 1742215Notes

Reaction equation

HRID 1742215 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:9][CH:8]=1>[OH-].[Na+]>[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 8002Butyl bromideHCID 19008989HCID 19008989, compound

Product 1

HCID 19008984HCID 19008984, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Excess 1-bromobutane was added to a mixture of 0.9 g of 4-[3-(4-hydroxyphenyl)propyl]pyridine in 10 mL of 2N NaOH, and the mixture was refluxed for several hours. Then the mixture was cooled and the pH adjusted to 10. The product was extracted with CH2Cl2. The CH2Cl2 layer was then separated, washed with fresh water, filtered through phase separating paper, and concentrated. The residue was adsorbed onto silica gel and chromatographed over silica gel eluting with CH2Cl2 >15% EtOAc/CH2Cl2. Yield 0.45 g.

Workup

  1. temperaturethe mixture was refluxed for several hours
  2. temperatureThen the mixture was cooled
  3. extractionThe product was extracted with CH2Cl2
  4. customThe CH2Cl2 layer was then separated
  5. washwashed with fresh water
  6. filtrationfiltered through phase
  7. customseparating paper
  8. concentrationconcentrated
  9. customchromatographed over silica gel eluting with CH2Cl2 >15% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-7ddd9734ff6248ce9038e639c3bd878c
Source dataset
uspto-grants-1994_08
Patent number
US05338742

Reaction notes

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