2-Chloropyridine → HCID 15239098, compound

HRID 274350Notes

Reaction equation

HRID 274350 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:18])=[CH:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:3][C:4]([CH3:18])=[CH:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][O:15][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 79772-ChloropyridineHCID 24758Sodium hydrideHCID 15662576HCID 15662576, compound

Product 1

HCID 15239098HCID 15239098, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a mixture of sodium hydride (0.13 g) in 5 ml of THF and 5 ml of HMPA, cooled in an ice bath, is added, dropwise, 2-[4-(3-methyl-2-butenoxy)phenoxy]ethanol (1.00 g) in 5 ml of THF. The mixture is stirred at RT for 1 hour, after which 2-chloropyridine (0.61 g) is added and the mixture is stirred at 60° for 2 hours. The solvent is removed by rotoevaporation. The residue is taken up in ether, washed with water, dried and concentrated, and the remaining oil is purified by column chromatography to give 2-{2-[4-(3-methyl-2-butenoxy)phenoxy]ethoxy}pyridine, MS m/e 300 (M+).

Workup

  1. temperaturecooled in an ice bath
  2. additionis added
  3. stirringthe mixture is stirred at 60° for 2 hours
  4. customThe solvent is removed by rotoevaporation
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customthe remaining oil is purified by column chromatography

Sources & evidence

ORD record
ord-fe98b5c25dca4a7796ce8f0b2de28149
Source dataset
uspto-grants-1995_02
Patent number
US05389651

Reaction notes

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