HCID 22612037, compound → HCID 22612124, compound

HRID 844069Notes

Reaction equation

HRID 844069 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[C:12]([CH:13]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[OH:14])=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.CCCCCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:12]([C:13](=[O:14])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 22612037HCID 22612037, compoundHCID 131709961Jones' reagent

Product 1

HCID 22612124HCID 22612124, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

A solution of 353 mg (1.00 mmol) 2-(4-Fluorophenoxy)-a-[2-(4-methoxyphenyl)ethyl]-3-pyridinemethanol in 5 mL of acetone was cooled to 0° C. and treated with 1.6 mL (2.00 mmol) of 1.25 M Jones Reagent solution. The mixture was allowed to warm to rt and then quenched by the addition of 5 mL of isopropanol. The precipitate was removed by filtration, and the filtrate was evaporated and partitioned between 50 mL of saturated aqueous sodium hydrogencarbonate solution and 100 mL of EtOAc. The separated organic layer was combined with a 100 mL EtOAc backwash of the aqueous layer, washed with brine (50 mL), dried (Na2SO4), and evaporated. Trituration of the residue in hexane gave 271 mg (77% yield) of the title compound, mp 73-74° C. 1H NMR (CDCl3) d 3.03 (2H, t, J=7 Hz), 3.43 (2H, t, J=7 Hz), 3.78 (3H, s), 6.75-7.18 (9H, m), 8.17 (1H, dd, J=2.8 Hz), ), 8.25 (1H, dd, J=2.4 Hz); Anal. Calcd for C21H18NO3F.0.25 H2O; C, 70.87; H, 5.10; N, 3.94. Found: C, 70.88; H, 4.79; N, 3.79.

Workup

  1. customquenched by the addition of 5 mL of isopropanol
  2. customThe precipitate was removed by filtration
  3. customthe filtrate was evaporated
  4. custompartitioned between 50 mL of saturated aqueous sodium hydrogencarbonate solution and 100 mL of EtOAc
  5. washwashed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-19a3e8341eec4d00acb1c8036e1aa553
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…