Sodium Methoxide → 2-Methyl-2-(3,3,3-trifluoro-propylsulfanyl)-propionic acid ethyl ester

HRID 386920Notes

Reaction equation

HRID 386920 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]([S:8][C:9](=O)[CH3:10])([CH3:7])[CH3:6])[CH3:2].[F:13][C:14]([F:29])([F:28])CCOS(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]([CH3:7])([S:8][CH2:9][CH2:10][C:14]([F:29])([F:28])[F:13])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 126353403,3,3-Trifluoroprop-1-yl toluene-4-sulphonateHCID 57937863Ethyl 2-(acetylthio)-2-methylpropanoate

Product 1

HCID 592532102-Methyl-2-(3,3,3-trifluoro-propylsulfanyl)-propionic acid ethyl esterYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester (1.7 g, 8.72 mmol), toluene-4-sulfonic acid 3,3,3-trifluoro-propyl ester (2.3 g, 8.72 mmol) and sodium methoxide (1.9 g, 34.9 mmol) in ethanol (13 mL) are heated to 130° C. in a sealed tube for 4 h. The reaction is cooled to room temperature and concentrated under reduced pressure. The residue is diluted with DCM and washed with saturated aqueous NaHCO3 solution and brine. The organic layer is dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure to afford 1.76 g of title compound as a brown solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (3H, t, J=7 Hz), 1.51 (3H, s), 2.26-2.42 (2H, m), 2.76-2.85 (2H, m), 4.18 (2H, q, J=6.96 Hz)

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is diluted with DCM
  3. washwashed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8fe83ec184a2435e83ccf1961143b081
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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