Sodium borohydride → HCID 68182277, compound

HRID 1620260Notes

Reaction equation

HRID 1620260 reaction equation
[CH2:1]([C:3]1[C:12]([CH:13]=[O:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:15][CH3:16])[CH:9]=2)[N:4]=1)[CH3:2].[BH4-].[Na+]>C1COCC1>[CH2:1]([C:3]1[C:12]([CH2:13][OH:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:15][CH3:16])[CH:9]=2)[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86669828HCID 86669828, compound2×

Product 1

HCID 68182277HCID 68182277, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethyl-6-methoxyquinoline-3-carbaldehyde SMA 44004 (256 mg, 1.19 mmol) in THF (12 mL) in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (48 mg, 1.25 mmol) and the mixture was stirred for 2 h at RT, then quenched by careful addition of 2 N aqueous HCl (2.6 mL). After stirring for 30 min at RT, the mixture was basified with 2 N aqueous NaOH (2.6 mL) and THF was removed at 40° C. under vacuum. The residue was diluted with CH2Cl2 (50 mL) and the organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) gave (2-ethyl-6-methoxyquinolin-3-yl)-methanol SMA 44008 as a white solid (173 mg, 67% yield).

Workup

  1. customquenched by careful addition of 2 N aqueous HCl (2.6 mL)
  2. stirringAfter stirring for 30 min at RT
  3. customwas removed at 40° C. under vacuum
  4. additionThe residue was diluted with CH2Cl2 (50 mL)
  5. customthe organic phase was isolated
  6. washwashed with brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated at 40° C. under vacuum
  10. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50)

Sources & evidence

ORD record
ord-34f050d1923b4e8cb2fa58686bb42de1
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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