Triphenylphosphine → 2,3-Difluoro-6-nitro{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene

HRID 846326Notes

Reaction equation

HRID 846326 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[F:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[C:35]([N+:40]([O-:42])=[O:41])[C:34]=1[OH:43].[O:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[O:50][CH:51]([CH3:54])[CH2:52]O>O1CCCC1>[F:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[C:35]([N+:40]([O-:42])=[O:41])[C:34]=1[O:43][CH2:52][CH:51]([O:50][CH:45]1[CH2:46][CH2:47][CH2:48][CH2:49][O:44]1)[CH3:54]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5591501-Propanol, 2-[(tetrahydro-2H-pyran-2-yl)oxy]-HCID 27337452,3-Difluoro-6-nitrophenol

Product 1

HCID 146971782,3-Difluoro-6-nitro{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzeneYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.04 g of triphenylphosphine in 10 ml of anhydrous tetrahydrofuran was added dropwise 1.36 g of diethyl azodicarboxylate with stirring under cooling with ice, and the resulting mixture was stirred at the same temperature for 30 minutes. To this solution was added dropwise a solution of 1.05 g of 2,3-difluoro-6- nitrophenol (IV, Xa=Xb=F), 1.01 g of 2-O-(tetra-hydropyran-2-yl)propane-1,2-diol (III, Rc=THP) in 5 ml of anhydrous tetrahydrofuran and then the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and to the residue was added benzene and a saturated sodium bicarbonate aqueous solution. After the mixture was shaken, the organic layer was separated and washed successively with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The residue was purified through silica gel column to yield 1.85 g of the titled compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe resulting mixture was stirred at the same temperature for 30 minutes
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe solvent was removed under reduced pressure
  5. additionto the residue was added benzene
  6. stirringAfter the mixture was shaken
  7. customthe organic layer was separated
  8. washwashed successively with water
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified through silica gel column

Sources & evidence

ORD record
ord-e5fd9c415d124bcf869106eb13fdb254
Source dataset
uspto-grants-1992_08
Patent number
US05136059

Reaction notes

Loading…