Diethyl Ether → HCID 21290717, compound

HRID 623223Notes

Reaction equation

HRID 623223 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[Cl:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[Cl:15].[C:16]([O:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])#[C:17]C.C([O:29]CC)C>>[Cl:8][C:9]1[CH:10]=[C:11]([C:6]2[CH:7]=[C:17]([CH2:16][O:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])[O:29][N:3]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 72391,2-DichlorobenzeneHCID 8471TriethylamineHCID 57176700HCID 57176700, compound

Product 1

HCID 21290717HCID 21290717, compoundYield 87%

Procedure

2.02 g (0.02 mol) of triethylamine in 20 ml of diethyl ether were added dropwise over a period of 15 minutes at -10° C. to a solution of 4.49 g (0.02 mol) of 3,4-dichlorobenzene N-hydroxycarboximidoyl chloride in 90 ml of dry diethyl ether. After 0.5 hour at -5° C. to -10° C. 4.004 g (0.022 mol) of methyl 2-propynyloxy-2-methylpropionate were added and the mixture was stored at -5° C. for 48 hours. The mixture was filtered, the filtrate was evaporated and the residue was chromatographed on 150 g of silica gel using hexane/ethyl acetate (4:1) for the elution. There were obtained 6 g (87%) of pure methyl 2-[[3-(3,4-dichlorophenyl)-5-isoxazolyl]methoxy]-2-methylpropionate in the form of an oil.

Workup

  1. waitthe mixture was stored at -5° C. for 48 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customthe residue was chromatographed on 150 g of silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-114dc77fd1c2427db3de8dfbcd77f309
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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