HCID 19087772, compound → HCID 19087784, compound

HRID 1464370Notes

Reaction equation

HRID 1464370 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1)C(=C)C>CCN(C1C=CC=CC=1)CC>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[C:13]([O:15][CH3:16])=[O:14])=[CH:10][C:11]=1[CH2:10][C:9](=[CH2:8])[CH3:12]

Participants

3

Reactant 1

HCID 19087772HCID 19087772, compound

Product 1

HCID 19087784HCID 19087784, compound

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Conditions

Temperature
200 °C

Procedure

7.6 g (0.026 mol) of the compound from Example IV are dissolved in 50 ml of freshly distilled diethylaniline and the mixture is heated overnight at 200° C. (Claisen rearrangement). After cooling, the solvent is distilled off in vacuo, the residue is taken up in 200 ml of dichloromethane and the solution is washed twice with 40 ml of 2N hydrochloric acid in order to extract residues of diethylaniline. It is then washed until neutral, dried with sodium sulphate and concentrated to a small volume. Purification is carried out by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=9:1).

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent is distilled off in vacuo
  3. washthe solution is washed twice with 40 ml of 2N hydrochloric acid in order
  4. extractionto extract residues of diethylaniline
  5. washIt is then washed until neutral,
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated to a small volume
  8. customPurification

Sources & evidence

ORD record
ord-63c28c9e9c5548a1bc6068e1c757fde1
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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