Iodoethane → HCID 21949943, compound

HRID 2114642Notes

Reaction equation

HRID 2114642 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[O:5][C:6]1[C:7]([CH2:23][CH3:24])=[N:8][N:9]([CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[CH2:11][OH:12].[CH2:29](I)[CH3:30]>[Ag-]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[O:5][C:6]1[C:7]([CH2:23][CH3:24])=[N:8][N:9]([CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[C:10]=1[CH2:11][O:12][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 21949866HCID 21949866, compound

Product 1

HCID 21949943HCID 21949943, compound

Reagents, catalysts & solvents 1

HCID 178418778HCID 178418778, compoundCatalyst

Conditions

Temperature
40 °C

Procedure

Silver(I)oxide (210 mg, 0.900 mmol) was added in one portion to a stirred solution of the alcohol of Example 135 (129 mg, 0.300 mmol) in ethyl iodide (1.75 ml) at room temperature under nitrogen. The reaction was heated at 40° C. for 1 day and then cooled to room temperature. The mixture was filtered and the residual solid was washed with dichloromethane (10 ml). The filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume) to provide the title compound (60 mg) as a colourless oil.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered
  3. washthe residual solid was washed with dichloromethane (10 ml)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume)

Sources & evidence

ORD record
ord-f724e797821742728672fe279622949d
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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