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

HRID 497045Notes

Reaction equation

HRID 497045 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:32])([F:31])[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29]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][CH2:29][CH2:28][CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([C:19]([F:32])([F:18])[F:31])=[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 112067993-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propan-1-olHCID 114152013-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzene

Product 1

HCID 102177823-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of protective gas, 1.2 g of 3-acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzene, 0.9 g of 3-(5-trifluoromethylpyrid-2-yloxy)propan-1-ol and 1.12 g of triphenylphosphine were dissolved in 35 ml of dry tetrahydrofuran (THF). With ice-bath cooling, 0.74 g of diethyl azodicarboxylate was 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: 1.52 g (74%)

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-e2df113141a546ef87f6eadd86ed9e64
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

Loading…