Sodium Hydroxide → 2-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid

HRID 538631Notes

Reaction equation

HRID 538631 reaction equation
C([O:3][C:4](=[O:18])[C:5]([CH3:17])([S:7]([CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)(=[O:9])=[O:8])[CH3:6])C.[OH-].[Na+].CC(OC)(C)C>C1COCC1>[CH3:17][C:5]([S:7]([CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)(=[O:9])=[O:8])([CH3:6])[C:4]([OH:18])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 597039342-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid ethyl ester

Product 1

HCID 597039922-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 123 g (0.44 mol) of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid ethyl ester in THF (450 mL) are added 663 mL of 2M aq. NaOH solution (1.33 mol). The reaction is stirred at RT for 1 h. To the reaction mixture is added TBME (1.25 L) and the layers are separated. The aq. layer is cooled in an ice bath and then acidified with 37% aq. HCl solution (123 mL). The resulting precipitate is isolated by filtration, washed with water (200 mL) and dried under reduced pressure at 50° C. to afford 101 g of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid. Yield: 91%; ESI-MS: 251 [M+H]+

Workup

  1. customthe layers are separated
  2. temperatureThe aq. layer is cooled in an ice bath
  3. customThe resulting precipitate is isolated by filtration
  4. washwashed with water (200 mL)
  5. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-8071bf908a894145ab7d1c5df5a20563
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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