Pyridine → 2-Acetyl-5-methoxy-3-oxo-pentanoic acid methyl ester

HRID 1242469Notes

Reaction equation

HRID 1242469 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5](=[O:10])[CH2:6][CH2:7][O:8][CH3:9].[Cl-].[Mg+2].[Cl-].N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>ClCCl>[CH3:1][O:2][C:3](=[O:11])[CH:4]([C:21](=[O:23])[CH3:22])[C:5](=[O:10])[CH2:6][CH2:7][O:8][CH3:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 542416Methyl 5-methoxy-3-oxopentanoateHCID 5360315Magnesium Chloride

Product 1

HCID 860465112-Acetyl-5-methoxy-3-oxo-pentanoic acid methyl esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of 5.28 g (32.96 mmol) 5-methoxy-3-oxo-pentanoic acid methyl ester and 3.14 g (32.96 mmol) anhydrous magnesium chloride in 50 ml dichloromethane was dropped within 3 min 5.3 ml (65.92 mmol) pyridine. 3.27 ml (34.61 mmol) of acetic anhydride was then added within 3 min. The reaction mixture was stirred over night at RT and after concentration under reduced pressure it was partitioned between ether, 1N HCl and water. The ether solution was concentrated under reduced pressure to give 5.87 g pure 2-acetyl-5-methoxy-3-oxo-pentanoic acid methyl ester.

Workup

  1. concentrationafter concentration under reduced pressure it
  2. customwas partitioned between ether, 1N HCl and water
  3. concentrationThe ether solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1331cf446e3d4a9399afb2165d35a886
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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