Lithium borohydride → HCID 90456052, compound

HRID 2202102Notes

Reaction equation

HRID 2202102 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][O:12][C:13]=2[C:14](OCC)=[O:15])=[CH:5][CH:4]=1)#[N:2].[Li+].[BH4-]>C1COCC1>[OH:15][CH2:14][C:13]1[O:12][CH:11]=[N:10][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 90456179HCID 90456179, compound

Product 1

HCID 90456052HCID 90456052, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-(4-cyanophenyl)-1,3-oxazole-5-carboxylate (347 mg, 1.43 mmol, 1.00 equiv) in anhydrous THF (5 mL) maintained at −5° C. was added LiBH4 (157 mg, 7.14 mmol, 4.98 equiv) in several portions. The resulting solution was stirred at room temperature for 3 h then quenched by the addition of 10 mL of saturated NH4Cl solution. The mixture was extracted with 2×10 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum to give 190 mg (66%) of 4-(5-(hydroxymethyl)oxazol-4-yl)benzonitrile as a yellow solid. LCMS (method D, ESI): RT=1.13 min, m/z=201.0 [M+H]+.

Workup

  1. customthen quenched by the addition of 10 mL of saturated NH4Cl solution
  2. extractionThe mixture was extracted with 2×10 mL of ethyl acetate
  3. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bd9fb9df87ee4e22a43321652c48b992
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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