Sodium Carbonate → HCID 86750873, compound

HRID 1781318Notes

Reaction equation

HRID 1781318 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[C:16](\[Cl:24])/[C:17]([O:19]C(C)(C)C)=[O:18])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].C(OC)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[C:16](\[Cl:24])/[C:17]([OH:19])=[O:18])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 15413tert-Butyl methyl etherHCID 86750874HCID 86750874, compound

Product 1

HCID 86750873HCID 86750873, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

29 g of methyl 2-methoxyimino-2-{2-[2-chloro-2-tert-butyloxycarbonyl-(Z)-ethenyl]phenyl}acetate from Example 3 are stirred in a mixture of 40 ml of trifluoroacetic acid and 160 ml of dichloromethane for 2.5 hours at room temperature. The dark solution is then stirred into 500 ml of saturated sodium carbonate solution (pH 9). After the addition of 200 ml of methyl tert-butyl ether, the organic phase is separated off. The aqueous phase is again extracted with methyl tert-butyl ether and the pH is adjusted to 2-3 with 6N hydrochloric acid. The product separates out as an emulsion and is isolated by extracting three times with methyl tert-butyl ether and ethyl acetate. The combined organic phases are washed until neutral with saturated NaCl solution and dried over sodium sulfate. The solvent is removed, leaving 20 g of the title compound as a dark oil.

Workup

  1. customthe organic phase is separated off
  2. extractionThe aqueous phase is again extracted with methyl tert-butyl ether
  3. customis isolated
  4. extractionby extracting three times with methyl tert-butyl ether and ethyl acetate
  5. washThe combined organic phases are washed until neutral with saturated NaCl solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed

Sources & evidence

ORD record
ord-5ea1469a8e4446d8bece6f8a474dd542
Source dataset
uspto-grants-1997_05
Patent number
US05633268

Reaction notes

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