Water → HCID 49802030, compound

HRID 2406682Notes

Reaction equation

HRID 2406682 reaction equation
Br[C:2]1[C:3]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])(C)(C)C.[O:23]1[C:28](=[O:29])[CH2:27][CH2:26][CH2:25][C:24]1=[O:30].O>CCOCC>[CH2:12]([C:3]1[C:2]([C:28](=[O:29])[CH2:27][CH2:26][CH2:25][C:24]([OH:30])=[O:23])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7940Glutaric anhydrideHCID 66644054HCID 66644054, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 49802030HCID 49802030, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-100 °C

Procedure

To the solution of 3-bromo-2-hexyl-quinoline in ether was added tert-butyl lithium at −100° C. The reaction mixture was stirred for 2 hours at −100° C. To the reaction mixture a solution of dihydro-pyran-2,6-dione in ether was added at −100° C. and stirred for 30 minutes and was allowed to warm up to RT. The stirring was continued for 3 hours. The water was added to the reaction mixture and was stirred for 20 minutes. Solvent was evaporated under vacuum and water was added to the crude mixture. It was then acidified by using dilute HCl and was extracted with ether. The product was purified by column chromatography.

Workup

  1. stirringstirred for 30 minutes
  2. temperatureto warm up to RT
  3. waitThe stirring was continued for 3 hours
  4. stirringwas stirred for 20 minutes
  5. customSolvent was evaporated under vacuum and water
  6. additionwas added to the crude mixture
  7. extractionwas extracted with ether
  8. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-cfaec3304599485fafb17cdf9ca5525e
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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