Triethylamine → Tetralin

HRID 1825904Notes

Reaction equation

HRID 1825904 reaction equation
[C:1](Cl)(=O)[CH2:2][CH2:3][CH3:4].CCN([CH2:12][CH3:13])CC>C(Cl)Cl>[CH2:1]1[C:12]2[C:13](=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 8855Butyryl chloride

Product 1

HCID 8404TetralinYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 1 (0.2 g, 0.92 mmol) was reacted with butyryl chloride (0.14 g, 0.69 mmol) in 50 mL methylene chloride in the presence of Et3N chilled by an ice water bath. The reaction was continued for 3 hours and the solvent removed in vacua. The crude product was dissolved in ethyl acetate and extracted with saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, and chromatographed over a silica gel column. The pure compound was eluted with 1:4 EtOAc:hexane, yielding (R,S)-trans-7-methoxy-2-[N-(propynyl)-N-butyro)amino]tetralin in very good yield, 0.22 g (85% yield).

Workup

  1. temperaturechilled by an ice water bath
  2. customthe solvent removed in vacua
  3. dissolutionThe crude product was dissolved in ethyl acetate
  4. extractionextracted with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customchromatographed over a silica gel column
  7. washThe pure compound was eluted with 1:4 EtOAc

Sources & evidence

ORD record
ord-5b0b26f3097e4f3a9f327b6fefd6354a
Source dataset
uspto-grants-2006_05
Patent number
US07049337B2

Reaction notes

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