Pyridine → HCID 58287607, compound

HRID 73231Notes

Reaction equation

HRID 73231 reaction equation
[S:1]([O-:4])([O-])=[O:2].C.[Na+].[Na+].N1C=CC=C[CH:9]=1.Br[C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:18][C:16](=[O:17])[C:15]([S:1]([CH3:9])(=[O:4])=[O:2])([CH3:22])[CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 86619477Sodium methane sulfite

Product 1

HCID 58287607HCID 58287607, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 5 g (49 mmol) of sodium methane sulfite in DMF (50 mL) were added pyridine (6.3 mL) and ethyl α-bromoisobutyrate (2.9 mL). The reaction was stirred for 18 h at 50° C. under nitrogen. The reaction mixture was diluted with ethyl acetate (250 mL), washed with saturated aqueous NaHCO3 (2×100 mL), 2M aqueous HCl solution (50 mL), brine (1×50 mL) and dried over Na2SO4. Filtration, concentration under reduced pressure afforded 3.04 g of 2-methanesulfonyl-2-methyl-propionic acid ethyl ester.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×100 mL), 2M aqueous HCl solution (50 mL), brine (1×50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration, concentration under reduced pressure

Sources & evidence

ORD record
ord-3c3545b89e2e483a9c804767f70bcf54
Source dataset
uspto-grants-2014_09
Patent number
US08829034B2

Reaction notes

Loading…