Sodium Chloride → 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide

HRID 1375227Notes

Reaction equation

HRID 1375227 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:28])[C:10]([NH:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].S(C1C=CC(C)=CC=1)(O[C:33]#[C:34][CH3:35])(=O)=O.C[O-].[Na+].[Cl-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:28])[C:10]([NH:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:35][C:34]#[CH:33])=[C:21]([O:26][CH3:27])[CH:20]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 3715371-Propynyl 4-methylbenzenesulfonateHCID 10942334Sodium MethoxideHCID 115390922-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(4-hydroxy-3-methoxy-phenyl)-cyclohexyl]-acetamide

Product 1

HCID 116698222-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.6 g (1.4 mmol) of 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(4-hydroxy-3-methoxy-phenyl)-cyclohexyl]-acetamide and 0.4 g (1.9 mmol) of propynyl tosylate and 2.7 ml of 1 M solution of sodium methoxide in 10 ml methanol is heated to reflux for 3 hours. The reaction mixture is cooled and poured into 30 ml of aqueous saturated sodium chloride solution and finally extracted with two 100 ml portions of ethyl acetate. The combined organic extract is concentrated under reduced pressure to a residue, which is subjected to column chromatography on silica gel, with 1:1 ethyl acetate/isohexane as the eluant to obtain 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide.

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionfinally extracted with two 100 ml portions of ethyl acetate
  4. extractionThe combined organic extract
  5. concentrationis concentrated under reduced pressure to a residue, which

Sources & evidence

ORD record
ord-f0a44a4d6bff4268a68ed109467666ef
Source dataset
uspto-grants-2007_01
Patent number
US07166746B2

Reaction notes

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