2-Bromonaphthalene → HCID 22493510, compound

HRID 1816231Notes

Reaction equation

HRID 1816231 reaction equation
C([Li])CCC.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[C:19](=[O:25])[CH2:18]2.[OH-].[Na+]>C(OCC)C>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[C:19]1([OH:25])[CH:20]2[CH2:23][CH2:24][N:17]([CH2:22][CH2:21]2)[CH2:18]1

Participants

6

Reactant 4

HCID 113722-BromonaphthaleneHCID 14798Sodium HydroxideHCID 195073-QuinuclidinoneHCID 178418339Butyllithium

Product 1

HCID 22493510HCID 22493510, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

Butyllithium (31 ml, 72 mmol) was added to a mixture of 2-bromonaphthalene (14.9 g, 72.1 mmol) and diethyl ether (300 ml) at −70° C. The resulting mixture was stirred at −70° C. for 30 minutes. A mixture of 3-quinuclidinone and diethyl ether (150 ml) was added at −70° C. The mixture was stirred at −70° C. for 1 hour and was then allowed to reach room temperature. Aqueous sodium hydroxide (400 ml, 1 M) was added. The phases were separated and the aqueous phase was extracted with diethyl ether (100 ml). The combined organic phases were purified by chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 2.03 g (11%).

Workup

  1. additionwas added at −70° C
  2. stirringThe mixture was stirred at −70° C. for 1 hour
  3. customto reach room temperature
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with diethyl ether (100 ml)
  6. customThe combined organic phases were purified by chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1)

Sources & evidence

ORD record
ord-37253ce41fb14a26937687efc303c869
Source dataset
uspto-grants-2005_04
Patent number
US06884807B2

Reaction notes

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