Aluminium lithium hydride → HCID 22600035, compound

HRID 1759773Notes

Reaction equation

HRID 1759773 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:15](=O)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:15]([NH:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:24])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86588611HCID 86588611, compound

Product 1

HCID 22600035HCID 22600035, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of phenylacetic acid (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amide (7) (790 mg, 2.46 mmole) in 20 mL diethyl ether (ether) was treated with 400 mg of lithium aluminium hydride (LAH) and heated at reflux for 90 minutes. After cooling the reaction flask to 0° C., the reaction mixture was quenched by successive addition of 0.4 mL water, 0.4 mL of 15% aqueous sodium hydroxide solution and 1.2 mL water. The mixture was stirred at room temperature for 30 minutes and MgSO4 was added. After filtration, the mixture was concentrated in vacuo, to provide a pale yellow oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes), yielding 619 mg (82%) of phenethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (9) as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 90 minutes
  3. customthe reaction mixture was quenched by successive addition of 0.4 mL water, 0.4 mL of 15% aqueous sodium hydroxide solution and 1.2 mL water
  4. additionMgSO4 was added
  5. filtrationAfter filtration
  6. concentrationthe mixture was concentrated in vacuo
  7. customto provide a pale yellow oil
  8. customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0a88faa99bcc48ce895d84a3388fc1ff
Source dataset
uspto-grants-2005_01
Patent number
US06838472B2

Reaction notes

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