Triphenylphosphine → 2-Acetyl-6-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine

HRID 53211Notes

Reaction equation

HRID 53211 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][OH:13])[N:5]=1)(=[O:3])[CH3:2].[F:14][C:15]([F:31])([F:30])[C:16]1[O:20][N:19]=[C:18]([C:21]2[CH:26]=[C:25]([CH3:27])[C:24](O)=[C:23]([CH3:29])[CH:22]=2)[N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CN(C=O)C.O>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][O:13][C:24]2[C:23]([CH3:29])=[CH:22][C:21]([C:18]3[N:17]=[C:16]([C:15]([F:14])([F:31])[F:30])[O:20][N:19]=3)=[CH:26][C:25]=2[CH3:27])[N:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 190820072-Acetyl-6-(3-hydroxypropyl)-pyridineHCID 1355166662,6-Dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol

Product 1

HCID 190820492-Acetyl-6-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.1 g (0.55 mmol) of 2-acetyl-6-(3-hydroxypropyl)-pyridine, 0.14 g of 4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol, 0.175 g (1.2 eq) of triphenylphosphine in DMF under nitrogen at 0° C. was added dropwise a solution of 0.097 g (1.2 eq) of DEAD in DMF. The bright red solution was stirred at room temperature overnight, diluted with water, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated in vacuo, and the residue was purifed by MPLC to afford 2-acetyl-6-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-456664e7239c487e96fa20ede6f31d30
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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