Ethanol → HCID 14209149, compound

HRID 279779Notes

Reaction equation

HRID 279779 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[CH2:8][CH:7]1[CH2:11][C:12]([O:14]CC)=[O:13].C(O)C.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[CH2:8][CH:7]1[CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54369044HCID 54369044, compound

Product 1

HCID 14209149HCID 14209149, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.31 g (1 millimole) of ethyl [1-(2,4-dimethoxy-benzyl)-4-oxo-2-azetidinyl]-acetate and 4 ml of ethanol a solution of 0.04 g (1 millimole) of sodium hydroxide and 6 ml of water are added. The reaction mixture is stirred at room temperature for 2 hours. The solution is extracted three times with 3 ml of dichloromethane each. The aqueous layer is acidified with concentrated aqueous hydrochloric acid to pH 2 and extracted three times with 3 ml of dichloromethane each. The united organic layers are dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated. The residue is crystallized from benzene. Thus 0.27 g of the desired compound are obtained, yield: 88%, M.p.: 112° C.

Workup

  1. extractionThe solution is extracted three times with 3 ml of dichloromethane each
  2. extractionextracted three times with 3 ml of dichloromethane each
  3. dry with materialThe united organic layers are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. customThe residue is crystallized from benzene

Sources & evidence

ORD record
ord-ee76ee87ee8744208d54f8e3234bc2cf
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

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