1,6-Dibromohexane → HCID 23045258, compound

HRID 2108135Notes

Reaction equation

HRID 2108135 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.[OH-].[Na+]>O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 23045301HCID 23045301, compound

Product 1

HCID 23045258HCID 23045258, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[2-(2-pyridinyl)ethoxy]ethanol hydrochloride (1.55 g), 1,6-dibromohexane (5.94 g), TAB (0.5 g) and 50% sodium hydroxide (15 ml) was stirred at room temperature under nitrogen for 5 h. The mixture was diluted with water (100 ml), extracted with diethyl ether (2×150 ml) and evaporated in vacuo to give an oil. The residual oil was partitioned between 2N hydrochloric acid (100 ml) and hexane (2×100 ml). The aqueous phase was basified to pH12 with 50% sodium hydroxide, extracted with diethyl ether (2×150 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System F (2:1→1:1) gave the title compound (1.62 g) as a colourless oil. T.l.c. (diethyl ether) Rf 0.40

Workup

  1. extractionextracted with diethyl ether (2×150 ml)
  2. customevaporated in vacuo
  3. customto give an oil
  4. customThe residual oil was partitioned between 2N hydrochloric acid (100 ml) and hexane (2×100 ml)
  5. extractionextracted with diethyl ether (2×150 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customto give an oil
  9. customPurification by FCC
  10. washeluting with System F (2:1→1:1)

Sources & evidence

ORD record
ord-839757a177824c1c9fc2a814d9174815
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

Loading…