Triethylamine → 4-Cyclohexyl-7-methyl-1,2,3,4-tetrahydronaphth-1-one oxime

HRID 53135Notes

Reaction equation

HRID 53135 reaction equation
[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[C:10](=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl.[NH2:27][OH:28]>CO>[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[C:10](=[N:27][OH:28])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 102434644-Cyclohexyl 7-methyl-1,2,3,4-tetrahydronaphth-1-one

Product 1

HCID 851197614-Cyclohexyl-7-methyl-1,2,3,4-tetrahydronaphth-1-one oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 125 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 5.20 grams (21.49 mmol) 4-cyclohexyl 7-methyl-1,2,3,4-tetrahydronaphth-1-one, 54 mL methanol, 3.25 grams (32.23 mmol) triethylamine, and 2.22 grams (32.23 mmol) hydroxylamine hydrochloride. The reaction was stirred at room temperature for 1.5 days, evaporated, partitioned between ethyl acetate and water, and the aqueous layer extracted with fresh ethyl acetate. The combined organic layer was dried over sodium sulfate and evaporated to an oil, which was used directly.

Workup

  1. customTo a 125 mL round-bottomed flask equipped with condenser and nitrogen inlet
  2. customevaporated
  3. custompartitioned between ethyl acetate and water
  4. extractionthe aqueous layer extracted with fresh ethyl acetate
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. customevaporated to an oil, which

Sources & evidence

ORD record
ord-6fcda192c72444f68c9b740724f435e8
Source dataset
uspto-grants-1997_04
Patent number
US05618811

Reaction notes

Loading…