Ethanol → HCID 73828031, compound

HRID 2289442Notes

Reaction equation

HRID 2289442 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:16][C:10]2[S:11][C:12](C=O)=[CH:13][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.[NH2:18][OH:19].C(O)C.CCOC(C)=O>O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:16][C:10]2[S:11][C:12](=[N:18][OH:19])[CH2:13][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 21712698HCID 21712698, compound

Product 1

HCID 73828031HCID 73828031, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-ethoxycarbonyl-2-formyl-4,5,6,7-tetrahydrobenzo[b]thiophene (3.23 g), hydroxylamine hydrochloride (0.92 g), and ethanol (EtOH) (30 ml) was stirred at reflux for 30 minutes. The reaction mixture was added into a mixture of AcOEt and water. The separated organic layer was washed with water, and brine, and dried over MgSO4. After evaporation of the filtrate, the resulting precipitate was washed with a mixture of n-hexane and isopropyl ether to give 6-ethoxycarbonyl-2-hydroxyimino-4,5,6,7-tetrahydrobenzo[b]thiophene (1.81 g).

Workup

  1. temperatureat reflux for 30 minutes
  2. washThe separated organic layer was washed with water, and brine
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the filtrate
  5. washthe resulting precipitate was washed with a mixture of n-hexane and isopropyl ether

Sources & evidence

ORD record
ord-93c1e2c62ca94ff8ac1790139d2b0109
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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