Methanol → HCID 21939847, compound

HRID 1242907Notes

Reaction equation

HRID 1242907 reaction equation
[BH4-].[Na+].CO.[C:5]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[CH2:14][CH2:13][CH2:12]2)(=[O:7])[CH3:6].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:10]1[C:11]2[CH2:12][CH2:13][CH:14]=[CH:15][C:16]=2[CH:17]=[CH:18][C:9]=1[NH:8][C:5](=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamideHCID 4311764Sodium borohydride

Product 1

HCID 21939847HCID 21939847, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (931 mg, 24.6 mmol) was added to a methanol solution (60 ml) of 6-acetamido-1-tetralone (5.00 g, 24.6 mmol) under ice-cooling, which was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then, the solvent was distilled out under reduced pressure. p-Toluenesulfonic acid (468 mg, 2.46 mmol) and toluene (120 ml) were added to the obtained alcohol form (5.05 g, 24.6 mmol), which was stirred at 100° C. for 1 hour. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1), and powdered with hexane to give N-(7,8-dihydro-2-naphthalenyl)acetamide (3.17 g).

Workup

  1. temperaturecooling
  2. washwas washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled out under reduced pressure
  5. stirringwas stirred at 100° C. for 1 hour
  6. distillationThe solvent was distilled out under reduced pressure
  7. additionEthyl acetate was added to the residue, which
  8. washwas washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled out under reduced pressure
  11. customThe resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-60b1c88cfd684b15a4d8cb6f9648169b
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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