Ethyl Acetate → HCID 178477215, compound

HRID 1456351Notes

Reaction equation

HRID 1456351 reaction equation
[Si:1]([O:8][CH:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17]CS([O-])(=O)=O)[CH2:13][CH2:12]1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N-:23]=[N+:24]=[N-:25].[Na+].C(OCC)(=O)C>CN(C)C=O>[N:23]([CH2:17][C@H:14]1[CH2:15][CH2:16][C@H:11]([CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:10])[CH2:12][CH2:13]1)=[N+:24]=[N-:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 178477213HCID 178477213, compound

Product 1

HCID 178477215HCID 178477215, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

In 50 ml of dry dimethylformamide was suspended 2.0 g of trans-4-(1-t-butyldimethylsilyloxyethyl)cyclohexylmethylmethanesulfonate and 1.85 g of sodium azide, and the resulting mixture was stirred at 110° C. for 45 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, and the solvent was distilled off under reduced pressure to obtain 1.7 g of the desired compound as a pale yellow oil. This oil was used for the subsequentareaction 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-3fe9302b1051432ba0537323ddabe069
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

Loading…