Aluminum(III) Chloride → HCID 68567456, compound

HRID 747622Notes

Reaction equation

HRID 747622 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Cl-].[Cl-].[Al+3].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[C:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])(O)[CH3:20]>C1COCC1.C(OCC)C.C(OCC)(=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH2:11])=[C:13]([CH:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[CH3:20])[CH:14]=1

Participants

7

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 685682062-Amino-5-chloro-α-(2-chlorophenyl)-α-methylbenzenemethanol

Product 1

HCID 68567456HCID 68567456, compoundYield 23.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 54 ml of a 1M solution of lithium aluminium hydride in THF are added portionwise 7.1 g of aluminium trichloride. To this solution are added 4 g of 1-(2-amino-5-chlorophenyl)-1-(2-chlorophenyl)ethanol, obtained in Example 25.1, dissolved in diethyl ether, and the mixture is stirred for 18 hours at room temperature and then refluxed for 4 hours. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 40/60 (v/v) dichloromethane/cyclohexane mixture to give 0.9 g of the expected product.

Workup

  1. customobtained in Example 25.1
  2. temperaturerefluxed for 4 hours
  3. washwashed with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on a column of silica gel
  7. washeluting with a 40/60 (v/v) dichloromethane/cyclohexane mixture

Sources & evidence

ORD record
ord-0c94a5d8e00b4f9690466198946b3818
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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