Aluminium lithium hydride → HCID 86695925, compound

HRID 2369522Notes

Reaction equation

HRID 2369522 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O-])=[O:15])=[CH:12][N:11]=[CH:10][C:9]=2[F:17])=[C:4]([F:18])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([F:17])=[CH:10][N:11]=[CH:12][C:13]=2[CH2:14][OH:15])=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86695926HCID 86695926, compound

Product 1

HCID 86695925HCID 86695925, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(4-chloro-2-fluorophenyl)-5-fluoronicotinate (300 mg, 1.058 mmol) in tetrahydrofuran (7 mL) cooled to 0° C. was added LAH (0.441 mL, 1.058 mmol) in THF dropwise and the solution was stirred for 30 min. The reaction was then warmed to room temperature and stirred for 12 h. The reaction was quenched with saturated aqueous ammonium chloride (5 mL) and extracted with ethyl acetate (2×5 mL). The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure to afford (4-(4-chloro-2-fluorophenyl)-5-fluoropyridin-3-yl)methanol (200 mg, 0.782 mmol, 74% yield) as a pale brown oil. LCMS (ESI) m/e 255.9 [(M+H)+, calcd for C12H9ClF2NO 256.0]; LC/MS retention time (Method F): tR=0.89 min.

Workup

  1. stirringstirred for 12 h
  2. customThe reaction was quenched with saturated aqueous ammonium chloride (5 mL)
  3. extractionextracted with ethyl acetate (2×5 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4be85ea158a44d0aa2764513fce12758
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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