Pyridine → HCID 18319513, compound

HRID 1699392Notes

Reaction equation

HRID 1699392 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].O[CH2:8][C:9]1[C:19]2[O:18][CH2:17][CH2:16][C:15]([C:20]([O:22][CH3:23])=[O:21])=[CH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1.C(OCC)(=O)C>ClCCl.O>[Cl:2][CH2:8][C:9]1[C:19]2[O:18][CH2:17][CH2:16][C:15]([C:20]([O:22][CH3:23])=[O:21])=[CH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24819Phosphorus pentachlorideHCID 18319582HCID 18319582, compound

Product 1

HCID 18319513HCID 18319513, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, phosphorus pentachloride (1.6 g) was added to a mixture of methyl 2,3-dihydro-9-hydroxymethyl-1-benzoxepin-4-carboxylate (1.2 g) and pyridine (0.62 ml) in dichloromethane (24 ml) under ice-cooling and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added a mixture of ethyl acetate and water. The separated organic layer was washed with saturated aqueous sodium bicarbonate and water. The organic layer was dried over magnesium sulfate and evaporated in vacuo to give methyl 2,3-dihydro-9-chloromethyl-1-benzoxepin-4-carboxylate (1.19 g) as an oil.

Workup

  1. temperaturecooling
  2. additionTo the reaction mixture was added
  3. washThe separated organic layer was washed with saturated aqueous sodium bicarbonate and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4efd4229a6c84a6296a04116b64cef6e
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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