Iodoethane → HCID 70023179, compound

HRID 1168297Notes

Reaction equation

HRID 1168297 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[CH:17]=[N:16][NH: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[CH:17]=[N:16][N:15]([CH2:25][CH3:26])[N:14]=2)[O:4]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 59094519HCID 59094519, compound

Product 1

HCID 70023179HCID 70023179, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2H-1,2,3-triazole (Preparation 23) (0.35 g, 1.45 mmol), potassium carbonate (0.2 g, 1.45 mmol) and iodoethane (0.12 ml, 1.45 mmol) in acetone (5 ml) was stirred at room temperature for 48 hours. The reaction mixture was allowed to cool to room temperature, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99.7:0.3 by volume) gradually changing to dichloromethane:methanol (99:1 by volume) to give initially 4-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-ethyl-2H-1,2,3-triazole (0.18 g) followed by the title compound (TLC data—Rf 0.25 in solvent system dichloromethane:methanol 98:2 by volume) contaminated with 25% of 5-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-ethyl-1H-1,2,3-triazole (0.16 g). This material was used in subsequent steps without further purification.

Workup

  1. filtrationfiltered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99.7:0.3 by volume)

Sources & evidence

ORD record
ord-ff7cc1939680419d8ab1b003c622cb8b
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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