Lithium borohydride → HCID 67517566, compound

HRID 1519548Notes

Reaction equation

HRID 1519548 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]([F:13])[C:6]=1[Cl:14].[BH4-].[Li+]>C1COCC1>[Cl:14][C:6]1[C:7]([F:13])=[C:8]([CH:9]=[CH:10][C:5]=1[CH2:4][CH2:3][OH:2])[C:11]#[N:12]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86694462HCID 86694462, compound

Product 1

HCID 67517566HCID 67517566, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyl(2-chloro-4-cyano-3-fluorophenyl)acetate (400 mg, 1.8 mmol) in THF (5 mL) was treated with lithium borohydride solution in THF (2M, 1.1 mL, 2.2 mmol) and the reaction was stirred overnight at room temperature. The reaction was quenched with 2N HCl and the mixture was partitioned with ethyl acetate and water. The aqueous was extracted again with ethyl acetate and the organic layers were washed with brine, dried over sodium sulfate and evaporated. The residue was purified on a CombiFlash Rf (24 gm, gradient 10-40% ethyl acetate in hexanes) to afford the title alcohol. 1H-NMR (500 MHz, CDCl3) δ ppm 1.66 (br s, 1H), 3.088 (t, J=6.4 Hz, 2H), 3.922 (t, J=6.4 Hz, 2H), 7.242 (d, J=8.1 Hz, 1H), 7.469 (dd, J=6.5 and 8.1 Hz, 1H).

Workup

  1. customThe reaction was quenched with 2N HCl
  2. customthe mixture was partitioned with ethyl acetate and water
  3. extractionThe aqueous was extracted again with ethyl acetate
  4. washthe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified on a CombiFlash Rf (24 gm, gradient 10-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6980283140b74153aba917637a07281b
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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