Hydrochloric Acid → HCID 21951793, compound

HRID 619683Notes

Reaction equation

HRID 619683 reaction equation
C([Li])CCC.Br[C:7]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[CH:16]([CH3:18])[CH3:17].[CH:19](N1CCCCC1)=[O:20].Cl>CCCCCC.O1CCCC1>[CH:16]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH:13]([CH3:15])[CH3:14])[C:7]=1[CH:19]=[O:20])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 121409152-Bromo-1,3-diisopropylbenzeneHCID 178418339Butyllithium

Product 1

HCID 21951793HCID 21951793, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

6.8 ml of a 1.6M solution of butyllithium in hexane was added dropwise at -78° C. while stirring to a solution of 2.6 g of 2-bromo-1,3-diisopropylbenzene in 16 ml of tetrahydrofuran. The mixture was stirred at the same temperature for 30 minutes and thereafter treated with a solution of 1.3 g of N-formylpiperdine in 1.5 ml of tetrahydrofuran. Thereafter, the mixture was left to warm to room temperature over a period of 6 hours. The mixture was cooled to 0° C. and treated with 12 ml of 3N hydrochloric acid. The aqueous solution was extracted four times with diethyl ether and the combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was chromatographed on silica gel with dichloromethane as the eluent and yielded 1.07 g of 2,6-diisopropylbenzaldehyde as an oil.

Workup

  1. waitThereafter, the mixture was left
  2. temperatureThe mixture was cooled to 0° C.
  3. extractionThe aqueous solution was extracted four times with diethyl ether
  4. washthe combined organic extracts were washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel with dichloromethane as the eluent

Sources & evidence

ORD record
ord-763953865e694fcabecefb58b788c587
Source dataset
uspto-grants-1999_09
Patent number
US05959113

Reaction notes

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