1,5-Dibromopentane → HCID 19876758, compound

HRID 1886019Notes

Reaction equation

HRID 1886019 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+]>ClCCl.O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 705322-Quinolineethanol

Product 1

HCID 19876758HCID 19876758, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-(2-Hydroxyethyl)quinoline (2.00 g), TAB (200 mg) and 1,5-dibromopentane (8 ml) were dissolved in dichloromethane (6 ml) and 50% aqueous sodium hydroxide (8 ml) added. The mixture was vigorously stirred at room temperature for 24 h, diluted with water (50 ml) and extracted with diethyl ether (2×30 ml). The organic extracts were dried, filtered and evaporated in vacuo to afford an oil, which was purified by FCC eluting with cyclohexane-ether (1:1) and ether, to give the title compound as a yellow oil (2.67 g), t.l.c. (ether) Rf 0.40.

Workup

  1. extractionextracted with diethyl ether (2×30 ml)
  2. customThe organic extracts were dried
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto afford an oil, which
  6. customwas purified by FCC
  7. washeluting with cyclohexane-ether (1:1) and ether

Sources & evidence

ORD record
ord-de49c383e5104b2fb0fecdec0f9ce81e
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

Loading…