HCID 53889921, compound → HCID 19606332, compound

HRID 1603937Notes

Reaction equation

HRID 1603937 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH2:16][OH:17])=[C:14]([F:20])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[C:14]([F:20])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 53889921HCID 53889921, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 19606332HCID 19606332, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-phenylbutoxy)-2-fluorobenzyl alcohol (1.38 g, 5.03 mmol) in dichloromethane (50 ml) was added with pyridinium chlorochromate (1.63 g, 7.54 mmol), stirring at room temperature for 1 h. After that the reaction mixture was filtered on celite, washing with dichloromethane. After drying and removing the solvent, the resulting crude was purified by chromatography through a silica gel column, eluting with dichloromethane, thereby recovering 1.02 g of the title compound (74% yield).

Workup

  1. filtrationAfter that the reaction mixture was filtered on celite
  2. washwashing with dichloromethane
  3. customAfter drying
  4. customremoving the solvent
  5. customthe resulting crude was purified by chromatography through a silica gel column
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-cc26687cb6744e78ab086a11239417bc
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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