Ethyl Acetate → HCID 178465656, compound

HRID 1456353Notes

Reaction equation

HRID 1456353 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16](OS(C)(=O)=O)[CH3:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16]([N:23]=[N+:24]=[N-:25])[CH3:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 178477159HCID 178477159, compound

Product 1

HCID 178465656HCID 178465656, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

In 50 ml of dry dimethylformamide were suspended 1.70 g of trans-4-benzyloxymethyl-1-(1-methanesulfonyloxyethyl)cyclohexane and 1.69 g of sodium azide, and the mixture was stirred at 110° C. for 30 minutes. To the reaction mixture were added 200 ml of ethyl acetate, and the mixture was washed three times with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.48 g of the desired compound as a pale yellow oil. This compound was used for the subsequent reaction without purification.

Workup

  1. washthe mixture was washed three times with an aqueous sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bd07de3ba9f44eafba2e4f21d7bc5dca
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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