HCID 131720048, compound → HCID 54169137, compound

HRID 1683999Notes

Reaction equation

HRID 1683999 reaction equation
[OH:1][CH:2]([CH3:12])[CH2:3][CH2:4][C@@H:5]([CH3:11])[CH2:6][C:7]([O:9][CH3:10])=[O:8].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:11][C@H:5]([CH2:4][CH2:3][C:2](=[O:1])[CH3:12])[CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 131720048HCID 131720048, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 54169137HCID 54169137, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol from Step 2 (293 mg) in CH2Cl2 (12 mL) was added a mixture of pyridinium chlorochromate (542 mg, 1.5 eq) and celite (542 mg). The suspension was stirred at r.t. overnight, and allowed to settle. The supernatant was collected and evaporated down to a residue which was chromatographed on silica gel, eluting with a 1:2 mixtue of EtOAc and hexane, to afford the desired ketone as a colorless liquid (189 mg).

Workup

  1. customThe supernatant was collected
  2. customevaporated down to a residue which
  3. customwas chromatographed on silica gel
  4. washeluting with a 1:2 mixtue of EtOAc and hexane

Sources & evidence

ORD record
ord-b8001e3045984df08e7d654ca49eddf7
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

Loading…