Water → HCID 18794887, compound

HRID 1004329Notes

Reaction equation

HRID 1004329 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:8][C:9]([CH3:11])=[O:10].Cl[CH2:19][C:20]1[O:24][C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][CH:21]=1.O>C(O)(C)(C)C>[CH2:28]([O:27][C:25]([C:23]1[O:24][C:20]([CH2:19][CH:8]([C:9](=[O:10])[CH3:11])[C:7]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:21][CH:22]=1)=[O:26])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 15538Tert-butyl acetoacetateHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18794887HCID 18794887, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 1.78 g of potassium tert-butoxide in 60 ml of tert-butyl alcohol was stirred together with 3.00 g of tert-butyl acetoacetate at 60° C. for 30 minutes under heating and then cooled to room temperature. 3.40 g of ethyl 5-(chloromethyl)-2-furancarboxylate was added dropwise, and the solution was stirred at room temperature for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=9/1→5/1] to give 2.26 g of the title compound as a colorless oily substance.

Workup

  1. temperatureunder heating
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=9/1→5/1]

Sources & evidence

ORD record
ord-ce460787e4c24c62ab8f4c9fdc5b0305
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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