Water → HCID 18794907, compound

HRID 1004333Notes

Reaction equation

HRID 1004333 reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Cl[CH2:15][C:16]1[O:17][C:18]([C:21](=[O:29])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:20]=1.O>O1CCCC1.C(OCC)(=O)C>[O:4]=[C:3]([CH3:5])[CH:2]([CH2:15][C:16]1[O:17][C:18]([C:21](=[O:29])[NH:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:20]=1)[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 15538Tert-butyl acetoacetateHCID 24758Sodium hydrideHCID 13515708HCID 13515708, compound

Product 1

HCID 18794907HCID 18794907, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 9.6 g of tert-butyl acetoacetate was dissolved in 80 ml of tetrahydrofuran, and 2.33 g of 60% oil sodium hydride was added under cooling with ice under stirring. The resulting solution was stirred at the same temperature for 10 minutes. After addition of 13.6 g of 2-(chloromethyl)-5-(phenylcarbamoyl)furan obtained in Reference Example 2 in 80 ml of tetrahydrofuran, the solution was stirred at room temperature for 10 minutes and then at 60° C. for 13 hours under heating. Water and ethyl acetate were added to the reaction solution for extraction, and the organic layer was washed with water, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride successively and then dried over anhydrous sodium 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=10/1→3/1] to give 14.0 g of the title compound as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe resulting solution was stirred at the same temperature for 10 minutes
  3. stirringthe solution was stirred at room temperature for 10 minutes
  4. washthe organic layer was washed with water, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1→3/1]

Sources & evidence

ORD record
ord-1595b079a2c34ae79c67c693941fa059
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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