Ammonia → HCID 10756943, compound

HRID 2397063Notes

Reaction equation

HRID 2397063 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:12]([CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[CH:13]=1.N.[H][H]>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:12]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 18986860HCID 18986860, compoundHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 10756943HCID 10756943, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

246 mg of aluminum lithium hydride was added under ice-cooling to a solution of 1.38 g of the crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyric acid in 20 ml of tetrahydrofuran and the resulting mixture was stirred at the same temperature for 30 minutes. Next, 25% aqueous ammonia was added thereto until no hydrogen evolved any more. After filtering with the use of Celite and anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:8) to give 0.86 g of 4-[5-chloro-2-(2-phenylethoxy)phenyl]butanol.

Workup

  1. filtrationAfter filtering with the use of Celite and anhydrous magnesium sulfate
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-480193610c7544b59de9e22318b119f6
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

Loading…