Aluminium lithium hydride → HCID 90456112, compound

HRID 2202122Notes

Reaction equation

HRID 2202122 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[CH:17][N:18]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:19]=2[C:20](OCC)=[O:21])=[CH:11][CH:10]=1)#[N:8]>C1COCC1>[OH:21][CH2:20][C:19]1[N:18]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:17]=[N:16][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90460781HCID 90460781, compound

Product 1

HCID 90456112HCID 90456112, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

To a solution of LiAlH4 (114 mg, 3.36 mmol, 3.00 equiv) in anhydrous THF (5 mL) maintained under nitrogen at −50° C. was added dropwise a solution of ethyl 4-(4-cyanophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-5-carboxylate (371 mg, 1.00 mmol, 1.00 equiv) in anhydrous THF (2 mL). The reaction was stirred at −50° C. for 1 h and then quenched by the addition of 1 mL of water. The resulting mixture was extracted with 4×20 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified on a silica gel column eluted with 0-50% of ethyl acetate in petroleum ether to give 110 mg (33%) of 4-(5-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)benzonitrile as a pale yellow solid. 1H-NMR (300 MHz, CDCl3): δ 7.92-7.85 (m, 2H), 7.71-7.65 (m, 3H), 5.39 (s, 2H), 4.79 (s, 2H), 3.56 (t, J=11.2 Hz, 2H), 0.94 (t, J=11.2 Hz, 2H), 0.01 (s, 9H) ppm. LCMS (method A, ESI): RT=1.27 min, m/z=330.0 [M+H]+.

Workup

  1. customquenched by the addition of 1 mL of water
  2. extractionThe resulting mixture was extracted with 4×20 mL of dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column
  6. washeluted with 0-50% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-9a296dcbc5264bd891597e8b6c335ca9
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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