Water → (2-t-Butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanone

HRID 1618898Notes

Reaction equation

HRID 1618898 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])[OH:12])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 68289423(2-t-Butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanol

Product 1

HCID 68289359(2-t-Butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanoneYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 0.32 g of (2-t-butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanol was dissolved in 3 ml of dichloromethane, 0.51 g of Dess-Martin reagent was added and the mixture was stirred for 1 hour at room temperature. After water was added and then the liquid was separated with ethyl acetate, the organic layer was concentrated and purified by silica gel column chromatography to obtain 0.21 g of (2-t-butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanone (Compound Number 57).

Workup

  1. customthe liquid was separated with ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-70f7d94e3e174567be1952eb89f77250
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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