2-Chloropyridine → 2-(2-{4-[(Butan-2-yl)oxy]phenoxy}propoxy)pyridine

HRID 274348Notes

Reaction equation

HRID 274348 reaction equation
[H-].[Na+].[CH3:3][CH:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:18])[CH2:16][CH3:17])=[CH:10][CH:9]=1)[CH2:5][OH:6].Cl[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:3][CH:4]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:15]([CH3:18])[CH2:16][CH3:17])=[CH:12][CH:13]=1)[CH2:5][O:6][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 3

HCID 79772-ChloropyridineHCID 24758Sodium hydrideHCID 156625782-{4-[(Butan-2-yl)oxy]phenoxy}propan-1-ol

Product 1

HCID 152390942-(2-{4-[(Butan-2-yl)oxy]phenoxy}propoxy)pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a mixture of sodium hydride (0.08 g) in 5 ml of tetrahydrofuran (THF) and 2 ml of hexamethylphosphoramide (HMPA), cooled in an ice bath, is added, dropwise, 2-methyl-2-[4-(1-methylpropoxy)phenoxy]ethanol (0.63 g). The mixture is stirred at RT for 2 hours, after which a solution of 2-chloropyridine (0.38 g) in 5 ml of THF is added and the mixture is stirred at 60° for 3 hours. The THF is then removed by rotoevaporation and the residue is purified by column chromatography on silica gel to give the product, 2-{2-methyl-2-[4-(1-methylpropoxy)phenoxy]ethoxy}pyridine, MS m/e 302 (M+).

Workup

  1. temperaturecooled in an ice bath
  2. additionis added
  3. stirringthe mixture is stirred at 60° for 3 hours
  4. customThe THF is then removed by rotoevaporation
  5. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-abefba7c21d548cf8df10c9700c80eab
Source dataset
uspto-grants-1995_02
Patent number
US05389651

Reaction notes

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