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

HRID 890468Notes

Reaction equation

HRID 890468 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9](=[O:17])[CH2:10][C:11](=[O:16])[CH2:12][CH2:13][O:14][CH3:15].[Cl-].[Mg+2].[Cl-].[C:21](OC(=O)C)(=[O:23])[CH3:22]>ClCCl>[CH3:7][O:8][C:9](=[O:17])[CH:10]([C:21](=[O:23])[CH3:22])[C:11](=[O:16])[CH2:12][CH2:13][O:14][CH3:15]

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%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (5.3 ml, 65.92 mmol) was dropped within 3 min to an ice cooled solution of 5-methoxy-3-oxo-pentanoic acid methyl ester (5.28 g, 32.96 mmol) and anhydrous magnesium chloride (3.14 g, 32.96 mmol) in dichloromethane (50 ml). Acetic anhydride (3.27 ml, 34.6 mmol) was added within 3 min. The reaction mixture was stirred over night at RT and after partial removal of the solvent under reduced pressure it was partitioned between ether and 1 N HCl/water. The ether solution was concentrated under reduced pressure to give 5.87 g (29 mmol, 88%) 2-acetyl-5-methoxy-3-oxo-pentanoic acid methyl ester.

Workup

  1. customafter partial removal of the solvent under reduced pressure it
  2. customwas partitioned between ether and 1 N HCl/water
  3. concentrationThe ether solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f18027dc00d04b069fec0028015cb366
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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