HCID 19982273, compound → HCID 53851287, compound

HRID 1460699Notes

Reaction equation

HRID 1460699 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH:27]=[O:28])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 19982273HCID 19982273, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 53851287HCID 53851287, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,4,5-Triphenyl-1H-pyrazol-1-butanol (4 g, 10.9 mmol) in dry CH2Cl2 (10 mL) was added to a stirred suspension of pyridinium chlorochromate (7.03 g, 32.6 mmol) in dry CH2Cl2 (370 mL). After 3 hours, the CH2Cl2 was removed in vacuo and the residue diluted with diethyl ether (800 mL) and filtered through diatomateous earth. The organic phase was washed twice with water and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated to furnish 3,4,5-triphenyl-1H-pyrazol-1-butanal as a viscous oil. MS(CI): m/e=367 (MH+)

Workup

  1. customthe CH2Cl2 was removed in vacuo
  2. additionthe residue diluted with diethyl ether (800 mL)
  3. filtrationfiltered through diatomateous earth
  4. washThe organic phase was washed twice with water and once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2f03157bd59444789f98140d70f5da0c
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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