Triphenylphosphine → HCID 19962069, compound

HRID 53202Notes

Reaction equation

HRID 53202 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.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28]O)=[CH:22][N:21]=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>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][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:22][N:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 140715693-(6-Chloropyridin-3-yl)propan-1-olHCID 1355166662,6-Dimethyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenol

Product 1

HCID 19962069HCID 19962069, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1.12 g (4.34 mmol) of 4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol, 0.87 g (1.2 eq) of 2-chloro-5-(3-hydroxypropyl)-pyridine, 1.4 g (1.2 eq) of triphenylphosphine in 50 ml of methylene chloride under nitrogen at 0° C. was added dropwise a solution of 0.86 g (1.2 eq) of DEAD in 5 ml of methylene chloride. The mixture was stirred under nitrogen at room temperature for 60 h, concentrated in vacuo and the residue was triturated with hexane/ethyl acetate, filtered, and the filtrate was concentrated in vacuo to yield a dark brown oil. The brown oil was purified by MPLC (50 id, Kieselgel 60 column, hexane/ethyl acetate, 3:1) to afford 1.4 g (78%) of 2-chloro-5-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine, as a white crystalline solid, m.p. 89°-91° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was triturated with hexane/ethyl acetate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto yield a dark brown oil
  6. customThe brown oil was purified by MPLC (50 id, Kieselgel 60 column, hexane/ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-11e67ddc3a724fc5b0de43993bbd3718
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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