Sodium borohydride → Methyl 3-cyano-4-isopropoxybenzoate

HRID 222923Notes

Reaction equation

HRID 222923 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[BH4-].[Na+].[CH2:16]1[CH2:20]OC[CH2:17]1.CO>>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:16]([CH3:20])[CH3:17])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 11769089Methyl 3-cyano-4-hydroxybenzoateHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 21956805Methyl 3-cyano-4-isopropoxybenzoateYield 99%

Procedure

To a solution of 3 (3.0 g, 10.8 mmol) in THF/MeOH (10 mL/10 mL) was slowly added NaBH4 (407 mg, 10.8 mmol). The mixture was stirred for 10 min, quenched by saturated NH4Cl and partitioned between EtOAc and H2O. The organic layer was washed with sat NaHCO3 and brine, dried over Na2SO4, filtered and concentrated to give 4 (3.0 g, 99%), which was used without further purification. LRMS (M+H+) m/z 281.0.

Workup

  1. customquenched by saturated NH4Cl
  2. custompartitioned between EtOAc and H2O
  3. washThe organic layer was washed with sat NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-78604694b7e44be4aedcfbf7d12cb56e
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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