Methyl 2-(4-(2-oxopropyl)phenoxy)acetate → Hydrochloric Acid

HRID 2309006Notes

Reaction equation

HRID 2309006 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[OH:17][CH2:18][CH2:19][O:20][CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=1)[CH2:22][NH2:23].[H][H].CC(C)=O.C(OCC)C>CO.[Pt]>[ClH:30].[ClH:30].[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:23][CH2:22][CH:21]([O:20][CH2:19][CH2:18][OH:17])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2]

Participants

8

Reactant 4

HCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetateHCID 20186751HCID 20186751, compoundHCID 21584533Acetone diethyletherHCID 178418361HCID 178418361, compound

Product 2

HCID 313Hydrochloric AcidHCID 70433870HCID 70433870, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

1-(4-Carbomethoxymethoxyphenyl)propan-2-one (4.4 g) and 2-(2-hydroxyethoxy)-2-(3-chlorophenyl)ethanamine (4.3 g) in methanol (100 ml) was hydrogenated in the presence of platinum (from platinum oxide, 50 mg) until hydrogen uptake ceased. The solution was filtered through diatomaceous earth, and the solvent removed under vacuum. Chromatography over silica gel in 2.5% methanol in dichloromethane gave an oil. Treatment of this oil with an ethereal solution of hydrogen chloride gave the title compound, mp 72°-75° C. (acetone-diethyl ether) as a 56:44 mixture of diastereoisomers.

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. customthe solvent removed under vacuum
  3. customChromatography over silica gel in 2.5% methanol in dichloromethane gave an oil

Sources & evidence

ORD record
ord-507bf915dd7147459e3ebab28c23d437
Source dataset
uspto-grants-1987_09
Patent number
US04692465

Reaction notes

Loading…