Lithium borohydride → HCID 90460321, compound

HRID 2202106Notes

Reaction equation

HRID 2202106 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]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[Li+].[BH4-]>C1COCC1>[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)[N:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 90460390HCID 90460390, compound

Product 1

HCID 90460321HCID 90460321, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(4-cyanophenyl)-1H-1,2,3-triazole-5-carboxylate (650 mg, 2.68 mmol, 1.00 equiv) in THF (15 mL) at 0° C. was added LiBH4 (177.3 mg, 8.06 mmol, 3.00 equiv) in portions. The resulting solution was stirred at room temperature for 3 h and then quenched with 100 mL of saturated NH4Cl solution. The mixture was extracted with 3×100 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-50% of ethyl acetate in petroleum ether to give 200 mg (37%) of 4-[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]benzonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.12 (d, J=8.0 Hz, 2H), 7.96 (d, J=8.0 Hz, 2H), 7.90 (s, 1H), 5.60 (t, J=5.2 Hz, 1H), 4.65 (d, J=5.2 Hz, 2H) ppm. LCMS (method A, ESI): RT=1.07 min, m/z=201.0 [M+H]+.

Workup

  1. customquenched with 100 mL of saturated NH4Cl solution
  2. extractionThe mixture was extracted with 3×100 mL of ethyl acetate
  3. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  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-06c8356f38424b0da2eb976e844ee8cc
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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