(-)-2-(4-(3-Hydroxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine → (-)-2-(4-(3-Butoxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

HRID 1735981

Reaction equation

HRID 1735981 reaction equation
[OH:1][CH:2]([C:28]([F:31])([F:30])[F:29])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:7][CH:6]=1>C(I)CCC.[Ag]=O>[CH2:28]([O:1][CH:2]([C:28]([F:30])([F:31])[F:29])[CH:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][N:12]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 54106197(-)-2-(4-(3-Hydroxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine

Product 1

HCID 54256226(-)-2-(4-(3-Butoxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidineYield 173.7%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 10962Butyl iodideSolvent

Procedure

1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine was dissolved in 5 ml of butyl iodide. The solution was added with 3 g of silver oxide and stirred at 25°-30° C. for 4 days. The reaction mixture was cleared of silver oxide by filtration and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 0.98 g of (-)-2-(4-(3-butoxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine.

Workup

  1. filtrationThe reaction mixture was cleared of silver oxide by filtration
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1ca4667f7f7442aa93f4e775435a2759
Source dataset
uspto-grants-1996_07
Patent number
US05539115

Linked notes

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