Aluminium lithium hydride → HCID 90460898, compound

HRID 2202110Notes

Reaction equation

HRID 2202110 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14](OCC)=[O:15])=[CH:12][N:11]=[CH:10]2)=[CH:5][CH:4]=1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[OH:15][CH2:14][C:13]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90460509HCID 90460509, compound

Product 1

HCID 90460898HCID 90460898, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a stirred solution of ethyl 1-(4-cyanophenyl)-1H-imidazole-5-carboxylate (50 mg, 0.21 mmol, 1.00 equiv) in anhydrous tetrahydrofuran (10 mL) maintained under nitrogen at −40° C. was added LiAlH4 (24 mg, 0.63 mmol, 3.05 equiv) in portions. The reaction was stirred at −40° C. for 1 h and then quenched by the addition of 2 mL of saturated aqueous NH4Cl solution. The solid was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified on a silica gel column eluted with 3.0-6.7% of methanol in dichloromethane to yield 36 mg (87%) of 4-(5-(hydroxymethyl)-1H-imidazol-1-yl)benzonitrile as a white solid. 1H-NMR (300 MHz, CDCl3): δ 10.11 (s, 1H), 8.07 (d, J=6.3 Hz, 2H), 7.85 (d, J=6.3 Hz, 2H), 7.77-7.72 (m, 4H), 7.24 (s, 1H), 4.63 (d, J=7.5 Hz, 2H) ppm. LCMS (method C, ESI): RT=0.25 min, m/z=200.0 [M+H]+.

Workup

  1. customquenched by the addition of 2 mL of saturated aqueous NH4Cl solution
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified on a silica gel column
  5. washeluted with 3.0-6.7% of methanol in dichloromethane

Sources & evidence

ORD record
ord-b7086c3205fd4e3abcd647585faf6763
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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