Triphenylphosphine → Methyl 3-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzoate

HRID 497047Notes

Reaction equation

HRID 497047 reaction equation
[Cl:1][C:2]1[C:3]([OH:18])=[C:4]([CH:9]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([Cl:17])[Cl:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:19][C:20]([F:33])([F:32])[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30]O)=[N:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[C:3]([O:18][CH2:30][CH2:29][CH2:28][O:27][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:33])([F:19])[F:32])=[CH:26][N:25]=2)=[C:4]([CH:9]=[C:10]([O:12][CH2:13][CH:14]=[C:15]([Cl:16])[Cl:17])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 112067993-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propan-1-olHCID 22318615Methyl 3-chloro-5-(3,3-dichloroallyloxy)-2-hydroxybenzoate

Product 1

HCID 22318619Methyl 3-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of protective gas, 1.85 g of methyl 3-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzoate, 1.3 g of 3-(5-trifluoromethylpyrid-2-yloxy)-propan-1-ol and 1.64 g of triphenylphosphine were dissolved in 50 ml of dry tetrahydrofuran (THF). With ice-bath cooling, 1.09 g of diethyl azodicarboxylate were added dropwise. After about 30 minutes, the ice-bath was removed, and the mixture was stirred at room temperature for 15 hours. The mixture was then concentrated under reduced pressure and the residue was taken up in a mixture of ethyl acetate and water. After shaking, the organic phase was isolated, dried and concentrated under reduced pressure. The crude product was purified chromatographically. Yield: 1.79 g (59%)

Workup

  1. temperatureWith ice-bath cooling
  2. customthe ice-bath was removed
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. additionthe residue was taken up in a mixture of ethyl acetate and water
  5. stirringAfter shaking
  6. customthe organic phase was isolated
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified chromatographically

Sources & evidence

ORD record
ord-75359f89be174903b9bf817cd5092295
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

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