Iodoethane → HCID 22341532, compound

HRID 584919Notes

Reaction equation

HRID 584919 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:13]=2)=[CH:8][CH:7]=1.[CH3:28][C:29](C)([O-])C.[K+].ICC>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]([CH2:28][CH3:29])[C:20](=[O:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:13]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 22341453HCID 22341453, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22341532HCID 22341532, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

600 mg (1.7 mmol) of N-(4′-[1,3]dioxolan-2-ylbiphenyl-3-ylmethyl)benzamide, 5 ml of THF and 206 mg (1.85 mmol) of potassium tert-butoxide are introduced into a three-necked flask under nitrogen. 300 μl 15 (3.7 mmol) of iodoethane are added dropwise. The reaction mixture is stirred at room temperature for 3 hours, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30). 400 mg (64%) of the desired product are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (70/30)

Sources & evidence

ORD record
ord-9a1ece62234543b0b7a1a9113a673af6
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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