Iodoethane → HCID 19352578, compound

HRID 725679Notes

Reaction equation

HRID 725679 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH:27]([OH:29])[CH3:28])=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:30](I)[CH3:31]>[Ag]=O.C(Cl)(Cl)Cl>[CH2:1]([O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH:27]([O:29][CH2:30][CH3:31])[CH3:28])=[CH:20][CH:21]=2)=[N:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 19352564HCID 19352564, compound

Product 1

HCID 19352578HCID 19352578, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6212ChloroformSolvent

Procedure

At room temperature, 1.6 g (4 mmol) of the (-)-5-octyloxy-2-{4-(6-hydroxy-1-trans-heptenyl)-phenyl}-pyrimidine obtained in Example 9, 20 ml of ethyl iodide and 2.8 g (12 mmol) of silver oxide were stirred for 60 hours, washed successively with 1N hydrochloric acid and saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture thus obtained was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.76 g (yield 43%) of (-)-5-octyloxy-2-{4-(6-ethoxy-1-trans-heptenyl)-phenyl}-pyrimidine, [α]D20 =-1.2 (c=0.95, CHCl3).

Workup

  1. washwashed successively with 1N hydrochloric acid and saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe reaction mixture thus obtained
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5c1384a58839431ab0f66f13c5f1c04e
Source dataset
uspto-grants-1998_01
Patent number
US05707547

Reaction notes

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