Diethyl Ether → HCID 13939036, compound

HRID 1073410Notes

Reaction equation

HRID 1073410 reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.[CH3:18][CH:19]([O:22][C:23]1[CH:32]=[CH:31][C:26]([O:27][CH2:28][CH2:29][OH:30])=[CH:25][CH:24]=1)[CH2:20][CH3:21].[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34].CCOCC>CN(C=O)C.O>[CH2:33]([NH:35][C:36](=[O:37])[O:30][CH2:29][CH2:28][O:27][C:26]1[CH:31]=[CH:32][C:23]([O:22][CH:19]([CH3:18])[CH2:20][CH3:21])=[CH:24][CH:25]=1)[CH3:34]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8022Ethyl isocyanateHCID 9798523Di-n-butyl diacetoxy tinHCID 13939035HCID 13939035, compound

Product 1

HCID 13939036HCID 13939036, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dibutyltin 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 (compound 30, Table A).

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-1c8e37922ac84d2fa68a8c98e063b911
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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