Water → 5-Chloro-alpha-(2-chlorophenyl)-2-(2,2,2-trifluoroethylamino)benzyl alcohol

HRID 1794Notes

Reaction equation

HRID 1794 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([NH:23][C:24](=O)[C:25]([F:28])([F:27])[F:26])=[C:12]([CH:22]=1)[CH:13]([OH:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20].O>C(OCC)C.O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([NH:23][CH2:24][C:25]([F:28])([F:26])[F:27])=[C:12]([CH:22]=1)[CH:13]([OH:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20]

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 539916235-Chloro-alpha-(2-chlorophenyl)-2-(trifluoroacetylamino)benzyl alcohol

Product 1

HCID 540071115-Chloro-alpha-(2-chlorophenyl)-2-(2,2,2-trifluoroethylamino)benzyl alcoholYield 86.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.25 g of lithium aluminum hydride in 20 ml of absolute ethyl ether, a solution of 1.2 g of 5-chloro-α-(2-chlorophenyl)-2-(trifluoroacetylamino)benzyl alcohol in 5 ml of tetrahydrofuran was added dropwise. After mixture stirring at room temperature for 1 hour, water was added, and the organic layer was dried, after which the solvent was removed and the residue was subjected to silica gel column chromatography to yield 1.0 g of an oily compound.

Workup

  1. customthe organic layer was dried
  2. customafter which the solvent was removed

Sources & evidence

ORD record
ord-043e8eba8ec84c2aabee85de8361dc19
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Reaction notes

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