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

HRID 53207
Notes
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Reaction equation

HRID 53207 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([OH:15])=[C:10]([CH3:16])[CH:9]=2)[N:4]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29]O)=[CH:23][N:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][O:15][C:11]2[C:12]([CH3:14])=[CH:13][C:8]([C:5]3[N:4]=[C:3]([C:2]([F:17])([F:1])[F:18])[O:7][N:6]=3)=[CH:9][C:10]=2[CH3:16])=[CH:23][N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 215852063-(6-Methoxypyridin-3-yl)propan-1-olHCID 1355166662,6-Dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol

Product 1

HCID 190820582-Methoxy-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.54 g (6 mmol) of 4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol, 1.2 g (1.2 eq) of 2-methoxy-5-(3-hydroxypropyl)-pyridine, 1.9 g (1.2 eq) of triphenylphosphine in 50 ml of methylene chloride under nitrogen at 5° C. was added in portions 1.22 g (1.2 eq) of DEAD. The mixture was stirred at room temperature for 20 h, concentrated in vacuo, the residue was triturated with ether, and filtered. The crude product was purified by MPLC (50 id, Kreselgel 60 column, hexane/ethyl acetate, 3:1) to afford 2 g (82%) of 2-methoxy-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine, as a clear oil, which upon recrystallization from isopropyl acetate/hexane afforded white powder, m.p. 62°-64° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was triturated with ether
  3. filtrationfiltered
  4. customThe crude product was purified by MPLC (50 id, Kreselgel 60 column, hexane/ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-e8beea17015d471c92c1ed6917af4195
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05618821

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes