HCID 14497596, compound → HCID 14497602, compound

HRID 373489Notes

Reaction equation

HRID 373489 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[N:22]=[C:21]([CH2:32][CH2:33][CH:34]([OH:36])[CH3:35])[CH:20]=2)=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[N:22]=[C:21]([CH2:32][CH2:33][C:34](=[O:36])[CH3:35])[CH:20]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14497596HCID 14497596, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 14497602HCID 14497602, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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-8d56dfd99cbc4977a6db21b88088ab20
Source dataset
uspto-grants-1992_11
Patent number
US05164381

Reaction notes

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