Iodoethane → HCID 59094511, compound

HRID 1168295Notes

Reaction equation

HRID 1168295 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]2[NH:17][CH:16]=[N:15][N:14]=2)[O:4]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH3:26]>CC(C)=O>[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]2[N:17]=[CH:16][N:15]([CH2:25][CH3:26])[N:14]=2)[O:4]1

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium Carbonate2×HCID 178496726HCID 178496726, compound

Product 1

HCID 59094511HCID 59094511, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4H-1,2,4-triazole (Preparation 20) (1.0 g, 4.2 mmol), potassium carbonate (0.57 g, 4.2 mmol) and iodoethane (0.33 ml, 4.2 mmol) in acetone (10 ml) was heated under reflux for one hour. Further iodoethane (0.05 ml, 0.6 mmol) and potassium carbonate (0.1 g, 0.7 mmol) were added and heating under reflux continued for 30 minutes. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane gradually changing to dichloromethane:methanol (97:3 by volume) to give the title compound (0.4 g) (TLC data—Rf 0.65 in solvent system dichloromethane:methanol 95:5 by volume).

Workup

  1. temperatureunder reflux for one hour
  2. temperatureheating
  3. temperatureunder reflux
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane

Sources & evidence

ORD record
ord-31cd17debb15445cb845e02141e42a61
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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