Sodium hydride → HCID 53894239, compound

HRID 2420048Notes

Reaction equation

HRID 2420048 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:12][OH:13])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[O:14]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+]>O1CCCC1>[O:14]([C:21]1[CH:22]=[C:23]([CH2:24][O:13][N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:9]([CH3:10])[CH3:11])[CH:26]=[CH:27][CH:28]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 71404683HCID 71404683, compound

Product 1

HCID 53894239HCID 53894239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.86 g of 1B, 5.2 g of 3-phenoxybenzyl bromide and 30 ml of tetrahydrofuran were mixed and 0.9 g of sodium hydride was added. The mixture was heated to 35°. The mixture was cooled, stirred at room temperature for 21 hours, then filtered, and the solvent was stripped from the filtrate. The liquid residue was chromatographed (silica gel, 1/2 v/v methylene chloride/pentane) to give (1C), 1-(4-chlorophenyl)-2-methyl-1-propanone O-((3-phenoxyphenyl)methyl)oxime as a light yellow liquid, boiling point not determined.

Workup

  1. temperatureThe mixture was heated to 35°
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe liquid residue was chromatographed (silica gel, 1/2 v/v methylene chloride/pentane)

Sources & evidence

ORD record
ord-6ff94dcf6560415fb1a5f5bf4913cd29
Source dataset
uspto-grants-1978_08
Patent number
US04108897

Reaction notes

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