Water → 2-[2-(4-Hydroxymethylphenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol

HRID 1901149Notes

Reaction equation

HRID 1901149 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:31]=[CH:30][C:14]([O:15][CH2:16][CH:17]([NH:19][CH2:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[OH:22])[CH3:18])=[CH:13][CH:12]=1)=O.O.[OH-].[Na+]>O1CCCC1>[OH:8][CH2:9][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH:17]([NH:19][CH2:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[OH:22])[CH3:18])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 218321732-[2-(4-Methoxycarbonylphenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol

Product 1

HCID 218321512-[2-(4-Hydroxymethylphenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanolYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.83 mg of lithium aluminum hydride was slowly added, with stirring, to a solution of 1.95 g of 2-[2-(4-methoxycarbonylphenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 1) dissolved in 70 ml of tetrahydrofuran, and the resulting mixture was allowed to react at room temperature for 2 hours. At the end of this time, 0.9 ml of water, 0.9 ml of a 15% w/v aqueous solution of sodium hydroxide and 3 ml of water were added, in that order, to the reaction mixture, and the resulting mixture was stirred at room temperature. The reaction mixture was then filtered using a Celite (trade mark) filter aid, and the filtrate was freed from the solvent by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and ethanol as the eluent, to give 1.5 g of the title compound as a glass-like material, having an Rf=0.55 (thin layer chromatography over silica gel, using a 4:1 by volume mixture of ethyl acetate and ethanol as the developing solvent).

Workup

  1. customto react at room temperature for 2 hours
  2. filtrationThe reaction mixture was then filtered
  3. filtrationfilter aid
  4. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and ethanol as the eluent

Sources & evidence

ORD record
ord-230324a1174c4e9281c5e20857571c0e
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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