Water → 2-(3,4-Dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide

HRID 992443Notes

Reaction equation

HRID 992443 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:24])[C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:25](Br)[C:26]#[CH:27].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:24])[C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:27][C:26]#[CH:25])=[C:17]([O:22][CH3:23])[CH:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 117730892-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide

Product 1

HCID 117741762-(3,4-Dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-(3,4-dichloro-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide, propargyl bromide (0.5 ml) and potassium carbonate (1.5 g) in dimethyl sulfoxide is stirred at +80° C. for 3 hours. The mixture is cooled to room temperature and water (150 ml) is added. The mixture is extracted with ethyl acetate (2×200 ml) and washed with brine (100 ml). The organic layers are collected, dried with MgSO4 and evaporated. 2-(3,4-Dichloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide is obtained which is purified by flash column chromatography on silica gel (ethyl acetate/hexane 2:1); the product is an oil.

Workup

  1. extractionThe mixture is extracted with ethyl acetate (2×200 ml)
  2. washwashed with brine (100 ml)
  3. customThe organic layers are collected
  4. dry with materialdried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-0b408455c9594d5daeae371b3b3a5026
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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