1-Piperidinecarboxaldehyde → 3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxaldehyde

HRID 1836860Notes

Reaction equation

HRID 1836860 reaction equation
C([Li])CCC.[CH:6](N1CCCCC1)=[O:7].Br[C:15]1[C:24]([CH3:25])=[CH:23][C:22]2[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=2[CH:16]=1.[Cl-].[NH4+]>O1CCCC1>[CH:6]([C:15]1[C:24]([CH3:25])=[CH:23][C:22]2[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=2[CH:16]=1)=[O:7]

Participants

6

Reactant 4

HCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 100393466-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Product 1

HCID 2266983,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxaldehydeYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

22.2 mL (35.2 mmol) of n-butyl lithium (1.6 M in hexanes) was added. After 1 hours, a solution of 3.95 mL (35.5 mmol) of N-formylpiperidine was added to a solution of 5 g (17.8 mmol) of 2-bromo-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 50 mL of tetrahydrofuran, cooled in a dry ice/acetone bath. After 30 minutes 30 mL of saturated aqueous ammonium chloride was added to the reaction mixture. The reaction mixture was warmed to room temperature and extracted with ethyl acetate. The organic phase was separated, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with gradient elution (hexane-10% ethyl acetate/hexane) to provide 3.5 g (85%) of 2-formyl-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (m.p.: 82.4-84.1° C.).

Workup

  1. temperaturecooled in a dry ice/acetone bath
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel with gradient elution (hexane-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3c5b9ccbb7474d50b14af40283898248
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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