Dichloromethane → HCID 14497602, compound

HRID 1761567Notes

Reaction equation

HRID 1761567 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[CH:23][CH:22]=[N:21]2)=[CH:16][CH:15]=1.[CH2:25]([Cl:27])Cl>>[Cl:27][C:25]1[CH:11]=[CH:10][C:9]([C:24]2[N:20]([C:17]3[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=3)[N:21]=[C:22]([CH2:16][CH2:15][C:14](=[O:13])[CH3:19])[CH:23]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 122381311-(4-Methoxyphenyl)-1H-pyrazoleHCID 178418287HCID 178418287, compound

Product 1

HCID 14497602HCID 14497602, compoundYield 70%

Procedure

To a suspension of pyridinium chlorochromate (3.65 g, 16.93 mM) in CH2Cl2 (20 ml) was added the alcohol 20, (3.02 g, 8.46 mM) in CH2Cl2 (15 ml). After stirring for 4 hours, the reaction solution was decanted from the chromium precipitates that were washed with EtOAc (2×150 ml). The reaction solution and the washes were combined, filtered through florosil, and concentrated in vacuo. Chromatography (120 g, Baker 40 gm silica gel) with Et2O:hexane (1:1 to 100% Et2O) as eluent, followed by crystallization from Et2O:hexane afforded 23, (2.09 g, 70%) as a white crystalline solid, mp=85°-86° C.

Workup

  1. customthe reaction solution was decanted from the chromium
  2. customprecipitates that
  3. washwere washed with EtOAc (2×150 ml)
  4. filtrationfiltered through florosil
  5. concentrationconcentrated in vacuo
  6. customChromatography (120 g, Baker 40 gm silica gel) with Et2O:hexane (1:1 to 100% Et2O) as eluent, followed by crystallization from Et2O

Sources & evidence

ORD record
ord-2b3440d828ef49398268287453576f5a
Source dataset
uspto-grants-1989_05
Patent number
US04826868

Reaction notes

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