Ammonium Chloride → 2-Acetyl-4,5-diisopropylfuran

HRID 1023712Notes

Reaction equation

HRID 1023712 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[O:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].[CH3:15][Li].[Cl-].[NH4+]>C(OCC)C>[C:12]([C:6]1[O:7][C:8]([CH:9]([CH3:10])[CH3:11])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)(=[O:14])[CH3:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 584205144,5-Diisopropylfuran-2-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 122588112-Acetyl-4,5-diisopropylfuranYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4,5-diisopropylfuran-2-carboxylic acid (196 mg, 1.00 mmol) in diethyl ether (6 ml) was cooled to −18° C., and added dropwise with methyllithium (1.2 M in Et2O, 2.5 ml, 3 mmol), and the mixture was stirred for 45 minutes. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The reaction mixture was treated in a conventional manner, and then the resultant was purified by silica gel chromatography [hexane-ethyl acetate (7:1)] to obtain the title compound (162 mg, 84%) as colorless oil.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. additionThe reaction mixture was treated in a conventional manner
  3. customthe resultant was purified by silica gel chromatography [hexane-ethyl acetate (7:1)]

Sources & evidence

ORD record
ord-b43d0001179b4140b41e57d861db6c71
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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