Water → HCID 67449947, compound

HRID 1505216Notes

Reaction equation

HRID 1505216 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[NH2:9][CH2:8][C:7]1[CH:10]=[CH:11][C:12]([C:14]([F:15])([F:16])[F:17])=[CH:13][C:6]=1[O:5][CH2:4][CH2:3][N:2]([CH3:18])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 67448006HCID 67448006, compound

Product 1

HCID 67449947HCID 67449947, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

The nitrile 26b (2.15 g, 8.33 mmol) solubilized in Et2O (20 mL) was added in small portion to a mixture of LiAlH4 (0.63 g, 2 mol eq) in Et2O (25 mL) stirred at 0° C. Then the mixture was stirred at room temperature overnight. The excess of LiAlH4 was decomposed by water addition at 0° C., the solid formed was filtered, washed with Et2O and the filtrate was separated. The organic phase was anhydrified over Na2SO4 and evaporated to dryness to obtain 27b as yellow oil (1.48 g, 5.64 mmol, 67% Yield) used without further purifications.

Workup

  1. stirringThen the mixture was stirred at room temperature overnight
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with Et2O
  5. customthe filtrate was separated
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-9d995661bce444139496e171aaabba38
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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