Potassium trimethylsilanolate → HCID 59267861, compound

HRID 553592Notes

Reaction equation

HRID 553592 reaction equation
C([O:3][C:4](=[O:19])[C:5]([CH3:18])([S:7]([CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)(=[O:9])=[O:8])[CH3:6])C.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH3:18][C:5]([S:7]([CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)(=[O:9])=[O:8])([CH3:6])[C:4]([OH:19])=[O:3]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 59268016HCID 59268016, compound

Product 1

HCID 59267861HCID 59267861, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.34 g (4.6 mmol) of 2-methyl-2-[2-(tetrahydro-pyran-4-yl)-ethanesulfonyl]-propionic acid ethyl ester in THF (40 mL) are added 1.17 g (9.2 mmol) of potassium trimethylsilanolate. The reaction is stirred at room temperature for 2 h. The solvent is removed under reduced pressure. The residue is partitioned between DCM (50 mL) and 1M aqueous HCl solution (10 mL). The aqueous layer is extracted with DCM (2×50 mL). The combined organic extracts are dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 1.02 g of 2-methyl-2-[2-(tetrahydro-pyran-4-yl)-ethanesulfonyl]-propionic acid. Yield: 84%, ES-MS: m/z 263 [M−H]

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe residue is partitioned between DCM (50 mL) and 1M aqueous HCl solution (10 mL)
  3. extractionThe aqueous layer is extracted with DCM (2×50 mL)
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d797f9fe6bb749cf95885612eed8465d
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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