Triphenylphosphine → 3-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[4-(5-trifluoromethylpyrid-2-yloxy)butyloxy]benzene

HRID 497049Notes

Reaction equation

HRID 497049 reaction equation
[C:1]([C:4]1[C:5]([OH:17])=[C:6]([Cl:16])[CH:7]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([Cl:15])[Cl:14])[CH:9]=1)(=[O:3])[CH3:2].[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30]O)=[N:24][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([C:4]1[C:5]([O:17][CH2:30][CH2:29][CH2:28][CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([C:19]([F:33])([F:18])[F:32])=[CH:25][N:24]=2)=[C:6]([Cl:16])[CH:7]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([Cl:15])[Cl:14])[CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 114152013-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzeneHCID 223186182-(4-Hydroxybutyloxy)-5-trifluoromethylpyridine

Product 1

HCID 223186263-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[4-(5-trifluoromethylpyrid-2-yloxy)butyloxy]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of protective gas, 0.1 g of 3-acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzene, 0.08 g of 4-(5-trifluoromethylpyrid-2-yloxy)butan-1-ol and 0.093 g triphenylphosphine were dissolved in 2 ml of dry tetrahydrofuran (THF). With ice-bath cooling, 56 μl 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: 0.051 g (35%)

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-9296e77940484e1cb130ab4d7d22df3c
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

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