Sodium hydride → Methyl 3-cyano-4-isopropoxybenzoate

HRID 222922Notes

Reaction equation

HRID 222922 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])#[N:4].BrCCO[Si]([C:23](C)([CH3:25])[CH3:24])(C)C>CN(C=O)C.CCOC(C)=O>[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH:23]([CH3:25])[CH3:24])[C:8]([O:10][CH3:11])=[O:9])#[N:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 21956805Methyl 3-cyano-4-isopropoxybenzoateYield 84.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (0.39 g, 9.3 mmol) in DMF (15 mL) was added a solution of 3 (1.9 g, 6.5 mmol) in DMF (10 mL) at 0° C. under nitrogen. The reaction was stirred for 1.5 h, and then (2-bromoethoxy)-tert-butyldimethylsilane (2.09 mL, 9.7 mmol) was added. The reaction mixture was stirred overnight, diluted with EtOAc, quenched with aqueous ammonium chloride solution, and extracted with EtOAc (3×50 mL). The organic layers were combined and dried over Na2SO4. Purification with over silica gel (EtOAc) gave the product 4 (1.2 g, 41%) as a light yellow solid.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customquenched with aqueous ammonium chloride solution
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. customPurification with over silica gel (EtOAc)

Sources & evidence

ORD record
ord-99a969d918784635b36871fb1112a870
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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