Iodoethane → HCID 18633446, compound

HRID 1085523Notes

Reaction equation

HRID 1085523 reaction equation
[CH2:1]([C:3]1[C:4](=[O:37])[NH:5][C:6](=[O:36])[N:7]([CH:35]=1)[C@@H:8]1[O:34][C@H:12]([CH2:13][O:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[OH-].[K+].[CH2:40](I)[CH3:41]>C1C=CC=CC=1.O1CCOCC1>[CH2:40]([O:11][C@@H:10]1[C@@H:12]([CH2:13][O:14][C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:34][C@@H:8]([N:7]2[CH:35]=[C:3]([CH2:1][CH3:2])[C:4](=[O:37])[NH:5][C:6]2=[O:36])[CH2:9]1)[CH3:41]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 13062021HCID 13062021, compound

Product 1

HCID 18633446HCID 18633446, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6 g of 2'-deoxy-5-ethyl-5'-O-trityluridine, 1.347 g of powdered potassium hydroxide and 1.95 ml of ethyl iodide in a mixture of 60 ml of benzene and 20 ml of dioxane was stirred and heated under reflux for 14 hours. The solvents were removed by evaporation, the residue was taken up in 6 ml of methanol and the solution was poured into 250 ml of water. The resulting mixture was extracted four times with 150 ml of chloroform each time and the combined chloroform extracts were evaporated to give 2'-deoxy-3'-O-ethyl-5-ethyl-5'-O-trityluridine which was used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 14 hours
  3. customThe solvents were removed by evaporation
  4. additionthe solution was poured into 250 ml of water
  5. extractionThe resulting mixture was extracted four times with 150 ml of chloroform each time
  6. customthe combined chloroform extracts were evaporated

Sources & evidence

ORD record
ord-6799f50e05244b939dafbbc6f8d6b94b
Source dataset
uspto-grants-1991_04
Patent number
US05010060

Reaction notes

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