Carbon Dioxide → HCID 15458596, compound

HRID 2270089Notes

Reaction equation

HRID 2270089 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[C:5]([C:13](O)(O)[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:25]([N:27](CC)[CH2:28][CH3:29])[CH3:26].C(=O)=O.S(Cl)(C)(=O)=O.C(NCC)C>CC(C)=O.C(Cl)(Cl)Cl.C(OCC)C>[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[C:5]([CH:13]([N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 8021DiethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18331358HCID 18331358, compound

Product 1

HCID 15458596HCID 15458596, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

1.04 g (3.15 mmol) of 2,3-dimethyl-8-(1-hydroxy-2-[tert-butyldimethylsilyloxy]-1-hydroxy-ethyl)quinoline, 20 ml of ethyl ether and 0.53 ml (3.77 mmol) of triethylamine are introduced into a 100 ml round-bottomed flask. The mixture is cooled to −30° C. by a bath of cardice in acetone and 0.30 ml (3.9 mmol) of mesyl chloride are added. The cooling bath is removed and the reaction mixture is allowed to warm to room temperature over 30 minutes. 100 ml of water are added and the resulting mixture is extracted with ethyl ether (3×100 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is transferred, without further purification, into a 25 ml three-necked flask fitted with a condenser. 6.5 ml (63 mmol) of diethylamine and 5 ml of chloroform are added and this mixture is refluxed for 16 hours. The reaction mixture is cooled to room temperature and concentrated under vacuum, 50 ml of water are added and the resulting mixture is extracted with ethyl acetate (3×50 ml). The organic phases are combined, dried over magnesium sulphate and concentrated under vacuum. The residue is purified by chromatography on a column of silica (elution solvent: 10% methanol in dichloromethane). 0.64 g (yield: 53%) of 2,3-dimethyl-8-(1-diethylamino-2-[tert-butyldimethylsilyloxy]ethyl)quinoline is obtained in the form of an oil.

Workup

  1. additionare added
  2. customThe cooling bath is removed
  3. addition100 ml of water are added
  4. extractionthe resulting mixture is extracted with ethyl ether (3×100 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue is transferred, without further purification, into a 25 ml three-necked flask
  8. customfitted with a condenser
  9. temperaturethis mixture is refluxed for 16 hours
  10. temperatureThe reaction mixture is cooled to room temperature
  11. concentrationconcentrated under vacuum, 50 ml of water
  12. additionare added
  13. extractionthe resulting mixture is extracted with ethyl acetate (3×50 ml)
  14. dry with materialdried over magnesium sulphate
  15. concentrationconcentrated under vacuum
  16. customThe residue is purified by chromatography on a column of silica (elution solvent: 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a035f329d38c43dc9a8f1507cfc2028f
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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