Hydrochloric Acid → 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-(tert-butoxycarbonylmethyl)oxime

HRID 2305034Notes

Reaction equation

HRID 2305034 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])[CH:17]=[C:16]([Cl:26])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12](=[N:14][OH:15])[CH3:13].[H-].[Na+].[H][H].Br[CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].Cl>COC(C)(C)C>[C:36]([O:35][C:33]([CH2:32][O:15][N:14]=[C:12]([CH2:11][O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1[C:2]([Cl:1])=[CH:19][C:18]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])=[CH:17][C:16]=1[Cl:26])[CH3:13])=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 865843985-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 540986435-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-(tert-butoxycarbonylmethyl)oxime

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

First, 0.45 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone oxime and 10 ml of tert-butyl methyl ether are placed in a reaction vessel, to which 48 mg of 60% sodium hydride (in oil) is slowly added with stirring at room temperature in a stream of nitrogen gas. The mixture is stirred at room temperature until the evolution of hydrogen gas ceases, to which 0.29 g of tert-butyl bromoacetate is added at room temperature, and the mixture is further stirred with heating under reflux. After completion of the reaction, the reaction mixture is poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product is subjected to silica gel chromatography, which affords 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-(tert-butoxycarbonylmethyl)oxime.

Workup

  1. additionis slowly added
  2. additionis added at room temperature
  3. stirringthe mixture is further stirred
  4. temperaturewith heating
  5. temperatureunder reflux
  6. customAfter completion of the reaction
  7. extractionextracted twice with diethyl ether
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customto give a crude product

Sources & evidence

ORD record
ord-7998bfff41a446d9996a1975b9baad71
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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