Ethanol → Ethyl 5-(4-(1-(hydroxyimino)ethyl)phenyl)-2-benzofurancarboxylate

HRID 2057974Notes

Reaction equation

HRID 2057974 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][C:14]=3[CH:23]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].C(O)C.Cl.[NH2:28][OH:29].C(=O)([O-])[O-].[Na+].[Na+]>O.O1CCCC1>[OH:29][N:28]=[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][C:14]=3[CH:23]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20329647Ethyl 5-(4-acetylphenyl)benzofuran-2-carboxylate

Product 1

HCID 73676876Ethyl 5-(4-(1-(hydroxyimino)ethyl)phenyl)-2-benzofurancarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.2 g of 10A, 100 ml of ethanol and 200 ml of tetrahydrofuran was heated to 60°-70° C. A solution of 1.53 g of hydroxylamine hydrochloride and 1.16 g of sodium carbonate in 20 ml of water was added. The mixture was heated for 3 hours at 60°-70° C. The resulting solid was collected, washed with water, then ethanol, and extracted with methylene chloride. The solvent was evaporated from the extract under reduced pressure to give ethyl 5-(4-(1-(hydroxyimino)ethyl)phenyl)-2-benzofurancarboxylate (12A), mp: 220°-222° C.

Workup

  1. temperaturewas heated to 60°-70° C
  2. temperatureThe mixture was heated for 3 hours at 60°-70° C
  3. customThe resulting solid was collected
  4. washwashed with water
  5. extractionethanol, and extracted with methylene chloride
  6. customThe solvent was evaporated from the
  7. extractionextract under reduced pressure

Sources & evidence

ORD record
ord-f7065bee2b854ba8ab9de5e1ee5e20c7
Source dataset
uspto-grants-1980_07
Patent number
US04213998

Reaction notes

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