3-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-ol → 3-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

HRID 29046Notes

Reaction equation

HRID 29046 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:19])[CH2:9][CH2:10][CH:11]2[O:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][O:12]2)=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[CH3:17][C:14]1([CH3:18])[CH2:13][O:12][CH:11]([CH2:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])[O:16][CH2:15]1

Participants

5

Reactant 2

HCID 107070143-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 106354633-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of α-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-propanol (Step 3) (2.6 g, 10.7 mmol) in methylene chloride (100 ml), pyridinium chlorochromate (3.5 g, 16.05 mmol) was added. After stirring at room temperature for 3 hr, the reaction mixture was diluted with ether and filtered through a short silica gel column. The column was eluted with ether and the fractions containing 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one were combined and concentrated (2.2 g, 85%): mp (DSC) 65° C. Anal Calc'd. for C15H19FO3: C, 67.65; H, 7.19. Found: C, 67.21; H, 7.43.

Workup

  1. filtrationfiltered through a short silica gel column
  2. washThe column was eluted with ether
  3. additionthe fractions containing 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one
  4. concentrationconcentrated (2.2 g, 85%)

Sources & evidence

ORD record
ord-ec4316e8173240f485047bee2424ebd5
Source dataset
uspto-grants-2008_09
Patent number
US07420061B2

Reaction notes

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