1-(3,5-Difluoro-2,4-dibenzyloxyphenyl)ethanol → 3',5'-Difluoro-2',4'-dibenzyloxyacetophenone

HRID 355411Notes

Reaction equation

HRID 355411 reaction equation
[F:1][C:2]1[C:3]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([CH:17]([OH:19])[CH3:18])[CH:5]=[C:6]([F:16])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[C:3]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([F:16])[C:7]=1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 189423411-(3,5-Difluoro-2,4-dibenzyloxyphenyl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 189423283',5'-Difluoro-2',4'-dibenzyloxyacetophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1.0M solution of Compound 24 in CH2Cl2 is added to a suspension of pyridinium chlorochromate (4.0 eq) in CH2Cl2 at 20° C. with stirring. The reaction is stirred for 24 hours and filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo and then purified by silica gel column chromatography (eluted with Hex/EtOAc) to yield Compound 25.

Workup

  1. stirringThe reaction is stirred for 24 hours
  2. filtrationfiltered through a pad of diatomaceous earth
  3. concentrationThe filtrate is concentrated in vacuo
  4. custompurified by silica gel column chromatography (eluted with Hex/EtOAc)

Sources & evidence

ORD record
ord-3f2121154c9e40cb9e0bd3c58c5a89e7
Source dataset
uspto-grants-1998_11
Patent number
US05830912

Reaction notes

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