Ammonia → HCID 18986932, compound

HRID 2397057Notes

Reaction equation

HRID 2397057 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:12]([CH2:14][CH2:15][C:16](OCC)=[O:17])[CH:13]=1.N.[H][H]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:12]([CH2:14][CH2:15][CH2:16][OH:17])[CH:13]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 18986901HCID 18986901, compoundHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 18986932HCID 18986932, compoundYield 35.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.84 g of aluminum lithium hydride was added to a solution of 10.76 g of the crude ethyl 3-[5-chloro-2-(2-phenylethoxy)phenyl]propionate in 100 ml of tetrahydrofuran under ice-cooling and the mixture was stirred at the same temperature for 1 hour. Then 25% aqueous ammonia was added thereto until no hydrogen gas evolved any more. After filtering with the use of Celite and anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:9) to give 3.31 g of 3-[5-chloro-2-(2-phenylethoxy)phenyl]propanol.

Workup

  1. temperaturecooling
  2. filtrationAfter filtering with the use of Celite and anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue thus obtained

Sources & evidence

ORD record
ord-d4eca556c70743348c314a453df48cca
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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