Acetone, oxime → HCID 15338607, compound

HRID 1456362Notes

Reaction equation

HRID 1456362 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].C([O-])(C)(C)C.[K+].F[C:13]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>CN(C)C=O>[CH3:1][C:2](=[N:4][O:5][C:13]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16])[CH3:3]

Participants

5

Reactant 3

HCID 67180Acetone, oximeHCID 113336284-(Benzyloxy)-2-fluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 15338607HCID 15338607, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7.83 g (0.107 mol) of acetone oxime in 200 ml of dimethylformamide is stirred for 30 minutes in the presence of 12 g (0.11 mol) of 95% potassium t-butanolate. A solution of 20.3 g (0.089 mol) of 2-fluoro-4-(phenylmethoxy)benzonitrile in 100 ml of dimethylformamide is then added over 15 minutes. The mixture is stirred for 2 hours and then poured into ice-water. The crystalline product is filtered off and dissolved in dichloromethane, and the solution is then dried over sodium sulphate and concentrated under reduced pressure. 21.2 g of product are obtained.

Workup

  1. filtrationThe crystalline product is filtered off
  2. dissolutiondissolved in dichloromethane
  3. dry with materialthe solution is then dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc9254ca174a4bb8ab9956fcd764dfce
Source dataset
uspto-grants-1998_12
Patent number
US05843975

Reaction notes

Loading…