Acetic Anhydride → HCID 136341639, compound

HRID 1964252Notes

Reaction equation

HRID 1964252 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-13069ac89c764fb9a97aeb99f3cca8a2
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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