Sodium Methoxide → HCID 59267977, compound

HRID 553591Notes

Reaction equation

HRID 553591 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:3][CH2:2]1.C[O-].[Na+].[CH2:23]([O:25][C:26](=[O:34])[C:27]([S:30]C(=O)C)([CH3:29])[CH3:28])[CH3:24]>C(O)C>[CH2:23]([O:25][C:26](=[O:34])[C:27]([CH3:29])([S:30][CH2:8][CH2:7][CH:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[CH3:28])[CH3:24]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 57937863Ethyl 2-(acetylthio)-2-methylpropanoateHCID 592679642-(tetrahydro-2H-pyran-4-yl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 59267977HCID 59267977, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 1.9 g (6.7 mmol) of toluene-4-sulfonic acid 2-(tetrahydro-pyran-4-yl)-ethyl ester in ethanol (20 mL) are added 1.4 g (26.8 mmol) of sodium methoxide, followed by 1.27 g (6.7 mmol) of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester. The reaction mixture is heated in a microwave at 130° C. for 0.5 h. The solvent is removed under reduced pressure. The residue is partitioned between saturated aqueous NaHCO3 solution (25 mL) and DCM (25 mL). The layers are separated and the aqueous phase extracted with DCM (2×25 mL). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 1.9 g of 2-methyl-2-[2-(tetrahydro-pyran-4-yl)-ethylsulfanyl]-propionic acid ethyl ester. Yield: 100%; ES-MS: m/z 261 [M+H]; 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 1.15-1.38 (5H, m), 1.42-1.70 (12H, m), 2.59-2.71 (1H, m), 3.37 (2H, td, J=11.73, 1.98 Hz), 3.95 (2H, ddd, J=11.04, 3.88, 0.91 Hz), 4.18 (2H, q, J=7.16 Hz)

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe residue is partitioned between saturated aqueous NaHCO3 solution (25 mL) and DCM (25 mL)
  3. customThe layers are separated
  4. extractionthe aqueous phase extracted with DCM (2×25 mL)
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-ac471472dbad440d83c5e1f4992dcd21
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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