Acetoacetic Acid → HCID 13939036, compound

HRID 2309829Notes

Reaction equation

HRID 2309829 reaction equation
CC(CC(O)=O)=O.[CH3:8][CH:9]([O:12][C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][CH2:19][OH:20])=[CH:15][CH:14]=1)[CH2:10][CH3:11].[CH2:23]([N:25]=[C:26]=[O:27])[CH3:24].CCOCC>CN(C=O)C.O>[CH2:23]([NH:25][C:26](=[O:27])[O:20][CH2:19][CH2:18][O:17][C:16]1[CH:21]=[CH:22][C:13]([O:12][CH:9]([CH3:8])[CH2:10][CH3:11])=[CH:14][CH:15]=1)[CH3:24]

Participants

7

Reactant 4

HCID 96Acetoacetic AcidHCID 3283Diethyl EtherHCID 8022Ethyl isocyanateHCID 13939035HCID 13939035, compound

Product 1

HCID 13939036HCID 13939036, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dibutylin diacetate (0.004 ml) is added to a solution of the above alcohol (0.42 g, 2.0 mmol) in 1.5 ml of DMF and the mixture is chilled in an ice bath. Ethyl isocyanate (0.18 ml, 2.2 mmol) is then added and the mixture is allowed to warm slowly to RT. The mixture is then poured into ether and water containing 10% potassium dihydrogen phosphate. The aqueous phase is extracted with ether, and the combined organic phases are washed with water and with brine, dried, filtered and the solvent is removed in vacuo to give O-2-[4-(1-methylpropoxy)phenoxy]ethyl N-ethylcarbamate.

Workup

  1. temperaturethe mixture is chilled in an ice bath
  2. extractionThe aqueous phase is extracted with ether
  3. washthe combined organic phases are washed with water and with brine
  4. customdried
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3485691bb3c341cebae3e65c10435f01
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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