Dimethylformamide → HCID 54392232, compound

HRID 1280197Notes

Reaction equation

HRID 1280197 reaction equation
[CH2:1]([C:3]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:16]=[C:15]([CH2:25][CH3:26])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=[N:13][OH:14])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CN(C)C=O>O>[CH2:33]([O:14][N:13]=[CH:12][CH2:11][O:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:4]1[C:15]([CH2:25][CH3:26])=[CH:16][C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:23])[Cl:24])=[CH:18][C:3]=1[CH2:1][CH3:2])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86584396HCID 86584396, compound

Product 1

HCID 54392232HCID 54392232, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 0.27 g of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde oxime, 0.10 g of potassium carbonate, 0.16 g of benzyl bromide, and 10 ml of N,N-dimethylformamide were placed in a reaction vessel. After stirring at room temperature for 24 hours, the reaction mixture was poured into water, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 0.21 g (yield, 56%) of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde O-benzyloxime, nD22.5 1.5402.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product

Sources & evidence

ORD record
ord-070202da5f79415197e379b369f1e8bb
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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