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

HRID 628765
Notes
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Reaction equation

HRID 628765 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028Tetrahydrofuran
Solvent

Procedure

To a solution of 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 aqueous sodium hydroxide solution (1.33 mol). The reaction is stirred at room temperature for 1 h. To the reaction mixture is added TBME (1.25 L) and the layers are separated. The aqueous layer is cooled in an ice bath and then acidified with 37% aqueous 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 as white crystalline solids. Yield: 91%; ES-MS: m/z 251 [M+H]; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31-1.45 (2 H, m), 1.49 (6 H, s), 1.70-1.79 (2 H, m), 2.13-2.28 (1 H, m), 3.24 (2 H, d, J=6.60 Hz), 3.28-3.38 (2 H, m), 3.76-3.85 (2 H, m), 13.65 (1 H, br. s.)

Workup

  1. customthe layers are separated
  2. temperatureThe aqueous 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-01789911407243b3ac7e89e3b30ec1f8
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09315454B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes