Acetic Anhydride → HCID 136341639, compound

HRID 1847367Notes

Reaction equation

HRID 1847367 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15](=[N:17][OH:18])[CH3:16])[CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[CH3:19][C:20](OC(C)=O)=[O:21]>>[C:20]([O:18]/[N:17]=[C:15](/[C:10]1[CH:9]=[C:8]([C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH2:6]2)[CH:13]=[CH:12][C:11]=1[OH:14])\[CH3:16])(=[O:21])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 136341637HCID 136341637, compound

Product 1

HCID 136341639HCID 136341639, compoundYield 99%

Procedure

The solution of 1-[4-hydroxy-3-(1-hydroxyimino-ethyl)-phenyl]-cyclopropanecarboxylic methyl ester (10.0 g, 40.1 mmol) in Ac2O (250 mL) was heated at 45° C. for 4 h. The Ac2O was removed by evaporation under vacuum before water (100 mL) and EtOAc (100 mL) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL×2). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give (E)-methyl 1-(3-(1-(acetoxyimino)ethyl)-4-hydroxyphenyl)cyclopropanecarboxylate (10.5 g, 99%), which was used in the next step without further purification.

Workup

  1. customThe Ac2O was removed by evaporation under vacuum before water (100 mL) and EtOAc (100 mL)
  2. additionwere added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (100 mL×2)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-919ed8e868684d1ebb05d00d33572a9b
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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