HCID 2797750, compound → HCID 45091016, compound

HRID 1935437Notes

Reaction equation

HRID 1935437 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=1[C:5](OCC)=[O:6])#[N:2].[Li+].[BH4-]>C1COCC1>[C:1]([C:3]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=1[CH2:5][OH:6])#[N:2]

Participants

4

Reactant 2

HCID 2797750HCID 2797750, compoundHCID 4148881Lithium borohydride2×

Product 1

HCID 45091016HCID 45091016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of ethyl 2-cyano-5-methoxybenzoate (5 g, 24 mmol) in THF (100 mL) at room temperature was added a solution of LiBH4 in THF (2M, 12 mL, 24 mmol). After 19 h, there was about 60% conversion of starting material. An additional quantity of LiBH4 in THF (2M, 12 mL, 24 mmol) was added and stirring continued for an additional 15 h. The solvent was removed under reduced pressure then water was carefully added to the residue. Excess hydride was destroyed by careful proportionwise addition of a saturated aqueous solution of NH4Cl. Once complete, the resulting mixture was extracted with ether and then with ethyl acetate. The combined extracts were dried over Na2SO4 and the solvents then removed in vacuo. The residue was purified by column chromatography eluting with 2:1:2 hexane/chloroform/ethyl acetate. The title compound was isolated as a white solid: 1H NMR (CDCl3) δ7.58 (d, J=8.5 Hz, 1H), 7.15 (d, J=2.7 Hz, 1H), 6.86 (dd, J=2.7, 8.5 Hz, 1H), 4.89 (d, J=6.0 Hz, 2H), 3.88 (s, 1H), 2.01 (t, J=6.0 Hz, 1H).

Workup

  1. waitcontinued for an additional 15 h
  2. customThe solvent was removed under reduced pressure
  3. additionwater was carefully added to the residue
  4. customExcess hydride was destroyed by careful proportionwise addition of a saturated aqueous solution of NH4Cl
  5. extractionOnce complete, the resulting mixture was extracted with ether
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. customthe solvents then removed in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluting with 2:1:2 hexane/chloroform/ethyl acetate

Sources & evidence

ORD record
ord-2572f517f8df410eb341b7e51faa200b
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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