Triethylamine → Cyclohexanecarbaldehyde oxime

HRID 2120086Notes

Reaction equation

HRID 2120086 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:10][OH:11].CCN(CC)CC>C(Cl)Cl>[CH:1]1([CH:7]=[N:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16275CyclohexanecarboxaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 638165Cyclohexanecarbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclohexanecarbaldehyde (4 ml, 33.02 mmol) in CH2Cl2 (100 ml) at room temperature was added hydroxylamine hydrochloride (2.76 g, 39.62 mmol) followed by Et3N (5.52 ml, 39.62 mmol) and the reaction was stirred overnight. The resulting mixture was partitioned between CH2Cl2 and H2O and the layers were separated. The organic layer was dried over Na2SO4, concentrated in vacuo and used directly for the next step. 1H NMR (CDCl3) δ 1.0-2.0 (m, 10H), 3.0 (m, 1H), 6.6 (d, 0.5H), 7.4 (d, 0.5H), 8.2 (bs, 1H).

Workup

  1. customThe resulting mixture was partitioned between CH2Cl2 and H2O
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bf212870d684af7b5e5fcc427eeb240
Source dataset
uspto-grants-2004_02
Patent number
US06689778B2

Reaction notes

Loading…