Ethyl propiolate → HCID 66759331, compound

HRID 880370Notes

Reaction equation

HRID 880370 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:4]=1[CH:21]=[N:22][OH:23].[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[C:25]#[CH:26].[O-]Cl.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[C:4]=1[C:21]1[CH:26]=[C:25]([C:24]([O:28][CH2:29][CH3:30])=[O:27])[O:23][N:22]=1

Participants

5

Reactant 3

HCID 12182Ethyl propiolateHCID 23665760Sodium HypochloriteHCID 86662377HCID 86662377, compound

Product 1

HCID 66759331HCID 66759331, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[2,4-dimethoxy-6-(4-nitrophenoxy)phenyl]-N-hydroxymethanimine (2.06 g, 6.7 mmol) and ethyl propiolate (3.28 mL, 32.4 mmol, 5 eq.) in DCM was slowly added drop wise 15% NaOCl solution (65 mL) at 0° C. After stirring overnight, the organic phase was separated and the aqueous was extracted twice with DCM. The organic phases were pooled and washed with 1 M Na2SO3 solution, then with brine and dried over Na2SO4. The solvent was removed and the residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 8/2 to provide the title compound (1.6 g, 57% yield)

Workup

  1. customat 0° C
  2. customthe organic phase was separated
  3. extractionthe aqueous was extracted twice with DCM
  4. washwashed with 1 M Na2SO3 solution
  5. dry with materialwith brine and dried over Na2SO4
  6. customThe solvent was removed
  7. customthe residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 8/2

Sources & evidence

ORD record
ord-956341e3da5f4bc0a6ead56ed76f68df
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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