1,6-Dibromohexane → HCID 22161756, compound

HRID 1088718Notes

Reaction equation

HRID 1088718 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:10]([CH2:15][CH2:16][CH2:17][OH:18])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.[OH-].[Na+]>O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:18][CH2:17][CH2:16][CH2:15][C:10]1[C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 22161757HCID 22161757, compound

Product 1

HCID 22161756HCID 22161756, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(phenylmethoxy)-2-pyridinepropanol (1.4 g), 1,6-dibromohexane (4 ml), 40% aqueous sodium hydroxide (4 ml) and TAB (100 mg) was stirred vigorously for 6 days. Water (10 ml) was added and the mixture was extracted with ether (3×10 ml). The ether extracts were washed with water and brine, dried and concentrated to an oil which was purified by FCC eluting with cyclohexane followed by cyclohexane/ethyl acetate (4:1) to give the title compound as an orange oil (1.0 g) t.l.c. (cyclohexane/ethyl acetate 4:1) Rf 0.25.

Workup

  1. extractionthe mixture was extracted with ether (3×10 ml)
  2. washThe ether extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated to an oil which
  5. customwas purified by FCC
  6. washeluting with cyclohexane

Sources & evidence

ORD record
ord-69e979fea55c438dac43a2bf133e00b9
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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