Aluminium lithium hydride → HCID 22481645, compound

HRID 2181700Notes

Reaction equation

HRID 2181700 reaction equation
[OH:1][C:2]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]([C:2]2([OH:1])[CH2:5][CH2:4][CH2:3]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 224816304-(1-Hydroxycyclobutyl)benzonitrile

Product 1

HCID 22481645HCID 22481645, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 250 mL flask was charged with 4.1 g (23.5 mmol) 4-(1-hydroxy-cyclobutyl)-benzonitrile and 100 mL anhydrous THF then cooled to 0° C. Next, 70.5 mL (70.5 mmol) 1M LiAlH4 was added dropwise. The reaction mixture was stirred at 0° C. for 10 minutes then heated to reflux for 30 minutes, then cooled to 0° C. and quenched with MeOH. Diluted with methylene chloride and washed with water (2×100 mL). The organic was filtered through Celite and concentrated to give 2 g of a yellow solid.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 30 minutes
  3. temperaturecooled to 0° C.
  4. customquenched with MeOH
  5. additionDiluted with methylene chloride
  6. washwashed with water (2×100 mL)
  7. filtrationThe organic was filtered through Celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a7413674804e4b13b47fc42e9f96193b
Source dataset
uspto-grants-2005_05
Patent number
US06894041B2

Reaction notes

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