Oxalyl chloride → HCID 11023860, compound

HRID 988951Notes

Reaction equation

HRID 988951 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12]([C:21]([OH:23])=[O:22])=[CH:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[C:24](Cl)(=O)C(Cl)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12]([C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 11099002HCID 11099002, compound2×

Product 1

HCID 11023860HCID 11023860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxyestra-1,3,5(10),16-tetraene-17-carboxylic acid (Compound J) (2.00 g) obtained according to the method described in Tetrahedron Letters, 26: 1109 (1985) was dissolved in dichloromethane (75 mL), and oxalyl chloride (2.3 mL) was added thereto under ice-cooling, followed by stirring at room temperature for 4 hours. After completion of the reaction, the reaction solution was concentrated, the residue was dissolved in dichloromethane (60 mL), and methanol (30 mL) and triethylamine (3.58 mL) were added thereto, followed by stirring at room temperature for 11.5 hours. After completion of the reaction, the reaction solution was concentrated, methanol (20 mL) and 2 mol/L hydrochloric acid (40 mL) were added to the residue, and the resulting precipitate was collected by filtration, and washed with 1 mol/L hydrochloric acid and then water, followed by drying under reduced pressure to give methyl 3-methoxyestra-1,3,5(10), 16-tetraene-17-carboxylate (2.01 g).

Workup

  1. temperatureunder ice-cooling
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated
  4. dissolutionthe residue was dissolved in dichloromethane (60 mL)
  5. additionmethanol (30 mL) and triethylamine (3.58 mL) were added
  6. stirringby stirring at room temperature for 11.5 hours
  7. customAfter completion of the reaction
  8. concentrationthe reaction solution was concentrated
  9. additionmethanol (20 mL) and 2 mol/L hydrochloric acid (40 mL) were added to the residue
  10. filtrationthe resulting precipitate was collected by filtration
  11. washwashed with 1 mol/L hydrochloric acid
  12. customby drying under reduced pressure

Sources & evidence

ORD record
ord-b4e17e1f61634b7e9207bc1697e4683e
Source dataset
uspto-grants-2003_10
Patent number
US06638923B2

Reaction notes

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