Ethanol → HCID 57968989, compound

HRID 1255624Notes

Reaction equation

HRID 1255624 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[B:16]([OH:17])[O:15][CH2:14][C:13]=3[CH:18]=2)=[C:6]([OH:21])[CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.O.[CH2:28](O)[CH3:29]>>[CH2:28]([O:2][C:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[B:16]([OH:17])[O:15][CH2:14][C:13]=3[CH:18]=2)=[C:6]([OH:21])[CH:5]=1)=[O:3])[CH3:29]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 57969215HCID 57969215, compound

Product 1

HCID 57968989HCID 57968989, compoundYield 77%

Procedure

A mixture of 5-(4-carboxy-2-hydroxyphenoxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1.95 g, 6.82 mmol) and sulfuric acid (1.5 mL) in ethanol (75 mL) was refluxed for 6 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure. Silica gel column (6:4 to 5:5 hexane/acetone) followed by recrystallization from diisopropyl ether gave 5-(4-Ethoxycarbonyl-2-hydroxyphenoxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1.65 g, 77%).

Workup

  1. temperaturewas refluxed for 6 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customSilica gel column (6:4 to 5:5 hexane/acetone) followed by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-ef87a45771e9453086c92c3a079b62e0
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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