Water → Methyl 3-oxo-2-propionylpentanoate

HRID 619309Notes

Reaction equation

HRID 619309 reaction equation
[H-].[Na+].[C:3](Cl)(=[O:6])[CH2:4][CH3:5].[OH2:8].S(=O)(=O)(O)O.C[CH2:15][O:16][CH2:17][CH3:18]>>[CH3:15][O:16][C:17]([CH:18]([C:3](=[O:6])[CH2:4][CH3:5])[C:3](=[O:6])[CH2:4][CH3:5])=[O:8]

Participants

6

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 62324Propionyl chloride

Product 1

HCID 21837307Methyl 3-oxo-2-propionylpentanoateYield 88%

Conditions

Temperature
5 °C

Procedure

A solution of 6.5 g (50 mmol) of methyl propionyl acetate in 100 mL of ether was treated with 1.19 g (50 mmol) of sodium hydride and the mixture was stirred for 2 hours. The mixture was then cooled to 5° C. and 6.93 g (6.51 mL. 75 mmol) of propionyl chloride was added dropwise over 5 minutes. The reaction mixture was stirred overnight at room temperature and then poured into cold water. This mixture was acidified with sulfuric acid and the product was extracted into ether, washed with water and dried. Evaporation gave the desired product, sufficiently pure for use in the following reaction, in 88% yield. 1H-NMR (CDCl3) δ1.08 (6H, t, J=7), 2.58 (4H, q, J=7), 3.66 (1H, s), 3.74 (3H, s).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionthe product was extracted into ether
  3. washwashed with water
  4. customdried
  5. customEvaporation

Sources & evidence

ORD record
ord-0eb3fa93a8324b969a8dc3f65a95464d
Source dataset
uspto-grants-1999_09
Patent number
US05958948

Reaction notes

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