Potassium trimethylsilanolate → HCID 59253288, compound

HRID 386861Notes

Reaction equation

HRID 386861 reaction equation
C[Si](C)(C)[O-].[K+].C([O:9][C:10](=[O:25])[C:11]([S:14]([CH:17]1[CH2:22][CH2:21][CH:20]([O:23][CH3:24])[CH2:19][CH2:18]1)(=[O:16])=[O:15])([CH3:13])[CH3:12])C>C1COCC1>[CH3:24][O:23][CH:20]1[CH2:21][CH2:22][CH:17]([S:14]([C:11]([CH3:13])([CH3:12])[C:10]([OH:25])=[O:9])(=[O:16])=[O:15])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 59253209HCID 59253209, compound

Product 1

HCID 59253288HCID 59253288, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium trimethylsilanolate (3.1 g, 24.65 mmol) is added to a solution of 2-(4-methoxy-cyclohexanesulfonyl)-2-methyl-propionic acid ethyl ester (3.6 g, 12.3 mmol) in 100 mL of THF. After stirring the reaction mixture at room temperature for 4 h, the solvent is removed under reduced pressure, saturated aqueous NaHCO3 solution is added and the mixtures is extracted with ethyl acetate. The two phases are separated and the aqueous layer is acidified with 2N aqueous HCl solution and extracted with ethyl acetate; the combined organic extracts are washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford 2.6 g of 2-(4-methoxy-cyclohexanesulfonyl)-2-methyl-propionic acid. Yield: 73%, over two steps. 1H-NMR (500 MHz, CHLOROFORM-d) δ ppm 1.21-1.37 (2H, m), 1.64-1.81 (8H, m), 2.19-2.32 (4H, m), 3.18-3.28 (1H, m), 3.40 (3H, s), 3.45 (1H, tt, J=11.96, 3.53 Hz); ES-MS: m/z 263 [M−H]

Workup

  1. customthe solvent is removed under reduced pressure, saturated aqueous NaHCO3 solution
  2. additionis added
  3. extractionthe mixtures is extracted with ethyl acetate
  4. customThe two phases are separated
  5. extractionextracted with ethyl acetate
  6. washthe combined organic extracts are washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dc3f803bd974541aec653592fbe4364
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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