Potassium trimethylsilanolate → HCID 59267861, compound

HRID 1802377Notes

Reaction equation

HRID 1802377 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-7fac08d3a21d4101b46031665183b5bf
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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