Lithium → HCID 19610253, compound

HRID 1602173Notes

Reaction equation

HRID 1602173 reaction equation
[Li].[C:2]1([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:13][CH:14]=[O:15])[CH2:9][CH2:10][C:11]#[N:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[NH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 19610222HCID 19610222, compound

Product 1

HCID 19610253HCID 19610253, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminumhydride (0.57 g. 15 mmol) in anhydrous THF (20 mL) was added carefully dropwise a solution of 4,4-diphenyl-5-formylpentanonitrile (1.96 g. 7.4 mmol) in anhydrous THF (20 mL). The mixture was stirred at rt for 1.5 hr. The reaction mixture was quenched by careful addition of SN NaOH (2.5 mL) and followed by water (1.5 mL). The mixture was stirred at room temperature for 10 min and then filtered and the solid was washed twice with diethylether. The organic filtrates were combined, dried (Na2SO4) and concentrated to give the desired product as solid foam (1.60 g, 80%): MS showed (M+H)+ (270; 1H-NMR (CDCl3, δ): 1.17-1.34 (m, 2H), 2.12-2.22 (m, 2H), 2.31-2.43 (m, 2H), 2.62-2.74 (m, 2H), 3.30-3.40 (m, 2H), 7.11-7.34 (m, 1OH).

Workup

  1. customThe reaction mixture was quenched by careful addition of SN NaOH (2.5 mL)
  2. stirringThe mixture was stirred at room temperature for 10 min
  3. filtrationfiltered
  4. washthe solid was washed twice with diethylether
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-49a33de4c4f8423388a77f56c7ca4ec0
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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