Dimethylformamide → 8-Formyl-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

HRID 274802Notes

Reaction equation

HRID 274802 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.C([Li])CCC.CCCCCC.CN(C)[CH:32]=[O:33]>O1CCCC1.O>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([CH:32]=[O:33])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Product 1

HCID 152304978-Formyl-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 8-bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene (1.68 gm, 5.4 mMol) in tetrahydrofuran (50 mL) at -78° C. was added a solution of n-butyl lithium in hexane (1.6 M, 5.4 mL, 8.6 mMol), and the solution was stirred for one hour at -78° C. To the solution was then added N,N-dimethylformamide (0.3 mL, 5.94 mMol), and the reaction mixture was allowed to warm gradually to room temperature. The reaction mixture was diluted with water (10 mL) and stirred vigorously for one-half hour. The reaction mixture was then extracted with chloroform. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated in vacuo to give a yellow-green oil. Purification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH) gave the title compound as a colorless oil (700 mg, 50%). The maleate salt was formed and crystallized (ethanol/diethyl ether) to give colorless crystals (m.p.=120°-121° C.).

Workup

  1. temperatureto warm gradually to room temperature
  2. stirringstirred vigorously for one-half hour
  3. extractionThe reaction mixture was then extracted with chloroform
  4. washThe combined extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customto give a yellow-green oil
  8. customPurification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH)

Sources & evidence

ORD record
ord-cb93866c9d8f41e0a4b7be8d4602fc3a
Source dataset
uspto-grants-1995_02
Patent number
US05389687

Reaction notes

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