Tetrahydrofuran → 2-(4-Methoxyphenyl)-5-octylpyridine

HRID 1768885Notes

Reaction equation

HRID 1768885 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C1COCC1.[CH2:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:21]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[N:6][CH:7]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 131283845-Bromo-2-(4-methoxyphenyl)pyridineHCID 178443577HCID 178443577, compound

Product 1

HCID 140699212-(4-Methoxyphenyl)-5-octylpyridine

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 962WaterSolvent

Procedure

To a flask containing 13A (1 g) and dichloro[1,3-bis (diphenylphosphino)propane]nickle(II) (15 mg, prepared as in Kumada et al., Org. Syn. Coll. Vol. VI, p 407) is added THF (11 ml) and octyl magnesium bromide (2M, 2.74 ml). The solution is refluxed for 16 hrs, then poured into water and extracted three times with ethyl acetate. The combined organic layers are washed with brine and dried over sodium sulfate, and the solvent is removed in vacuo.

Workup

  1. temperatureThe solution is refluxed for 16 hrs
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5567179e2e8049aca9efc6ec33cc0106
Source dataset
uspto-grants-1995_01
Patent number
US05380460

Reaction notes

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