Tetrahydrofuran → Methyl 3-cyano-4-isopropoxybenzoate

HRID 1621254Notes

Reaction equation

HRID 1621254 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>>[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 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

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

Procedure

To a solution of 3 (3.0 g, 10.8 mmol) in THF e H (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-b085afa00f194b299b31b25ee68e4b1b
Source dataset
uspto-grants-2014_07
Patent number
US08772507B2

Reaction notes

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