O-Methylhydroxylamine hydrochloride → 5-tert-butyl-1-indanone O-methyloxime

HRID 912629Notes

Reaction equation

HRID 912629 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=O)[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][O:17][NH2:18]>N1C=CC=CC=1>[CH3:16][O:17][N:18]=[C:10]1[C:11]2[C:7](=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13][CH:12]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 110305765-Tert-butyl-2,3-dihydroinden-1-one

Product 1

HCID 730474605-tert-butyl-1-indanone O-methyloxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-tert-Butyl-1-indanone (13.41 g, 71.23 mmol) and methoxyamine hydrochloride (6.68 g, 80 mmol) were disolved in pyridine (75 ml) and stirred at ambient temperature for 16 hours. The mixture was evaporated under reduced pressure and the residue was partitioned between water and diethyl ether (X2). The combined organic layers were washed with 1N aqueous hydrochloric acid, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was partitioned between water and diethyl ether (X2)
  3. washThe combined organic layers were washed with 1N aqueous hydrochloric acid
  4. dry with materialdried with magnesium sulfate
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-21d60427599a4c2cb94d0b704c1d126c
Source dataset
uspto-grants-2011_09
Patent number
US08026256B2

Reaction notes

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