Sodium Hydroxide → 2-Isopropyl-furan-3-carboxylic acid ethyl ester

HRID 490361Notes

Reaction equation

HRID 490361 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6](=[O:13])[CH2:7][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[CH3:4].Cl[CH:15](OCC)[CH2:16]Cl>O.C(OCC)C>[CH2:3]([O:5][C:6]([C:7]1[CH:16]=[CH:15][O:12][C:8]=1[CH:9]([CH3:10])[CH3:11])=[O:13])[CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79077Ethane, 1,2-dichloro-1-ethoxy-HCID 81583Ethyl isobutyrylacetate

Product 1

HCID 588241892-Isopropyl-furan-3-carboxylic acid ethyl esterYield 69.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

An ice-chilled solution of sodium hydroxide (1.9 g) in water (25 ml) was added, during 40 minutes, to a stirred solution of 4-methyl-3-oxo-pentanoic acid ethyl ester (3 g, 18.96 mmoles) and 1,2-dichloro-1-ethoxy-ethane (3.3 g, 35.19 mmole) in diethyl ether (15 ml) with ice bath cooling. When the addition was complete the mixture was stirred rapidly for 1 hour, then the ethereal layer was separated, washed with water and dried. Evaporation of the solvent gave a yellow oil, which was purified by flash chromatography using a gradient elution from neat pentane to pentane/diethyl ether 9:1 v/v as eluent, to afford compound 82 as an oil (2.4 g).

Workup

  1. temperaturecooling
  2. additionWhen the addition
  3. customthe ethereal layer was separated
  4. washwashed with water
  5. customdried
  6. customEvaporation of the solvent
  7. customgave a yellow oil, which
  8. customwas purified by flash chromatography
  9. washa gradient elution from neat pentane to pentane/diethyl ether 9:1 v/v as eluent

Sources & evidence

ORD record
ord-f2dfebbefa8e4cb1958f79b7d5d253d7
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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