Dimethylformamide → 2-Butynoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester

HRID 1078043Notes

Reaction equation

HRID 1078043 reaction equation
[Si:1]([O:8][CH2:9][C:10]#[C:11][C:12]([OH:14])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15]([O-])([O-])=O.[Na+].[Na+].CN([CH:24]=[O:25])C>CCOC(C)=O>[Si:1]([O:8][CH2:9][C:10]#[C:11][C:12]([O:25][CH2:24][CH3:15])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 224784454-{[tert-Butyl(dimethyl)silyl]oxy}but-2-ynoic acid

Product 1

HCID 114478792-Butynoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution/suspension of 2.0 g of 4-(t-butyldimethylsilyloxy)-2-butynoic acid and 1.48 g Na2CO3 in 37 mL DMF under N2 was added slowly 1.58 mL Et2SO4. After stirring overnight, the reaction was diluted with EtOAc and washed several times with H2O. The organic extract was then washed with brine and dried over MgSO4. Filtration, evaporation and flash chromatography with a 5%-10% Et2O/hexanes gradient provided 1.58 g of pure product.

Workup

  1. additionwas added slowly 1.58 mL Et2SO4
  2. washwashed several times with H2O
  3. extractionThe organic extract
  4. washwas then washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration, evaporation and flash chromatography with a 5%-10% Et2O/hexanes gradient

Sources & evidence

ORD record
ord-c31bfa1b817e478c976b93676f6b40ab
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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