Triphenylphosphine → HCID 89558677, compound

HRID 238390Notes

Reaction equation

HRID 238390 reaction equation
[I:1][C:2]1[C:3]([CH3:10])=[N:4][N:5]([CH3:9])[C:6]=1[CH2:7][OH:8].O[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.O1CCCC1>[I:1][C:2]1[C:3]([CH3:10])=[N:4][N:5]([CH3:9])[C:6]=1[CH2:7][O:8][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 71307692(4-iodo-2,5-dimethylpyrazol-3-yl)methanol

Product 1

HCID 89558677HCID 89558677, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (4-iodo-1,3-dimethyl-1H-pyrazol-5-yl)methanol (75 mg), 4-hydroxybenzotrifluoride (48 mg), 40% diisopropyl azodicarboxylate (90 mg, toluene solution), triphenylphosphine (117 mg) and tetrahydrofuran (3.0 mL) was stirred at a room temperature overnight. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=90:10 to 50:50), so as to obtain the title compound (34 mg) in the form of a light yellow solid.

Workup

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=90:10 to 50:50)

Sources & evidence

ORD record
ord-37dbc81db86142bab320338b348b42bd
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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