HCID 23087566, compound → HCID 131733451, compound

HRID 2278341Notes

Reaction equation

HRID 2278341 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:6][CH2:5]2.[CH3:19][O:20][C:21](=[O:27])[CH2:22][CH2:23][S:24]([O-:26])=[O:25].[Na+]>[Cu]I>[Si:12]([O:11][CH:7]1[C:8]2[C:4](=[CH:3][C:2]([S:24]([CH2:23][CH2:22][C:21]([O:20][CH3:19])=[O:27])(=[O:26])=[O:25])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 23087566HCID 23087566, compoundHCID 23665669Sodium 1-Methyl 3-Sulfinopropionate

Product 1

HCID 131733451HCID 131733451, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
110 °C

Procedure

[(5-bromo-2,3-dihydro-1H-inden-1-yl)oxy](tert-butyl)dimethylsilane (1.62 g, 4.95 mmol), sodium 3-methoxy-3-oxopropane-1-sulfinate (3.45 g, 19.8 mmol) and CuI (3.77 g, 19.8 mmol) were charged in a sealable microwave flask. The flask was closed and degassed twice, after which dry DMSO (10 mL) was added and the reaction mixture was degassed before being heated at 110° C. in an oil bath overnight. The reaction mixture was cooled and diluted with ethyl acetate (40 mL), filtered on a silica gel pad, and eluted with ethyl acetate. The organic solvents were concentrated under reduced pressure. The crude concentrate was purified on silica gel eluting with hexanes and ethyl acetate, then with DCM and methanol to afford the title compound.

Workup

  1. customThe flask was closed
  2. customdegassed twice
  3. additionafter which dry DMSO (10 mL) was added
  4. customthe reaction mixture was degassed
  5. temperatureThe reaction mixture was cooled
  6. additiondiluted with ethyl acetate (40 mL)
  7. filtrationfiltered on a silica gel pad
  8. washeluted with ethyl acetate
  9. concentrationThe organic solvents were concentrated under reduced pressure
  10. concentrationThe crude concentrate
  11. customwas purified on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-27e28fff100b448abd487b90a01332d1
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

Loading…