Ethanol → HCID 178465994, compound

HRID 1471852Notes

Reaction equation

HRID 1471852 reaction equation
[C:1]1([C:7]2[CH2:11][C:10](=[O:12])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13](O)[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CN1CCOCC1.O>[CH2:13]([O:12][C:10]1[NH:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1)[CH3:14]

Participants

7

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 785775-Phenyl-4H-pyrazol-3-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 178465994HCID 178465994, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 79724-MethylmorpholineSolvent

Procedure

To a solution of 3-phenyl-1H-pyrazol-5(4H)-one (1.0 g, 6.24 mmol), ethanol (0.288 g, 6.24 mmol) and triphenylphosphine (1.638 g, 6.24 mmol) in N-methylmorpholine (7 mL) was added diethylazo dicarboxylate (0.988 mL, 6.24 mmol) dropwise at 0° C. The reaction was warmed to room temperature and stirred for 2 h. The reaction was poured into H2O and extracted with ethyl acetate. The extract was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (0.89 g). LCMS m/z=189.19 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=4.2 Hz, 3H), 4.32 (q, J=4.2 Hz, 2H), 6.45 (s, 1H), 7.41-7.94 (m, 5H), 11.3 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e1d0b628169742f5abcfdebb0960479c
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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