Dichloromethane → HCID 21717619, compound

HRID 1859805Notes

Reaction equation

HRID 1859805 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.C(Cl)[Cl:21]>[OH-].[K+].CCO>[ClH:21].[CH:11]1(/[CH:12]=[C:14]2/[C:15](=[O:19])[C:16]3[C:11]([CH2:12][CH2:13]/2)=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:18][CH:17]=3)[CH2:16][CH2:17][CH2:18][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 21717619HCID 21717619, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 0.2 g (0.8 mmol) of 6-[2-(1H-1-imidazolyl)ethoxy]-1,2,3,4-tetrahydro-1-naphthalenone in 2 mL of 4% KOH in EtOH was treated with 0.1 mL (0.8 mmol) of cyclohexylaldehyde and the solution allowed to stir at room temperature for 3 days. The solution was diluted with CH2Cl2 and the layers separated. The CH2Cl2 was washed with saturated NaCl and dried over MgSO4. The CH2Cl2 was treated with HCl gas and the solvent removed. The residue was taken up in H2O and freeze-dried. There was obtained 35 mg (10% yield) of a hygroscopic solid. The structure was confirmed by mass spectroscopy. MS m/z 351 (m+H+).

Workup

  1. customthe layers separated
  2. washThe CH2Cl2 was washed with saturated NaCl
  3. dry with materialdried over MgSO4
  4. additionThe CH2Cl2 was treated with HCl gas
  5. customthe solvent removed
  6. customfreeze-dried

Sources & evidence

ORD record
ord-7c10ef9257ce4cb7b2e68123c766c8a0
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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