Dimethylformamide → Pentanoic acid, 2-acetyl-4-methyl-, ethyl ester

HRID 1427709Notes

Reaction equation

HRID 1427709 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CN(C=O)C.[H-].[Na+].[CH2:17](Br)[CH:18]([CH3:20])[CH3:19]>O>[C:3]([CH:2]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropaneHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydride

Product 1

HCID 538758Pentanoic acid, 2-acetyl-4-methyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 100 g (0.77 mol) of ethyl acetoacetate in 500 ml of DMF 30.7 g (0.77 mol) of 60% suspension of NaH in mineral oil was added in small portions by vigorous stirring at 60° C. This mixture was additionally stirred for 1 h, and then 105.5 g (0.77 mol) of isobutylbromide was added. The resulting mixture was stirred for 3 h at 90° C., then cooled to room temperature, and 1500 ml of cold water was added. The product was extracted by 3×300 ml of dichloromethane. The combined organic extract was evaporated at reduced pressure using rotary evaporator. Fractional rectification of the residue gave the title product, b.p. 75-80° C./4 mm Hg. Yield 80.5 g (56%).

Workup

  1. stirringThis mixture was additionally stirred for 1 h
  2. stirringThe resulting mixture was stirred for 3 h at 90° C.
  3. temperaturecooled to room temperature
  4. extractionThe product was extracted by 3×300 ml of dichloromethane
  5. extractionThe combined organic extract
  6. customwas evaporated at reduced pressure
  7. customevaporator

Sources & evidence

ORD record
ord-22664a7a7c674884aafc098002ad1237
Source dataset
uspto-grants-2015_01
Patent number
US08933256B2

Reaction notes

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