Methyl morpholine oxide → HCID 19611665, compound

HRID 1602394Notes

Reaction equation

HRID 1602394 reaction equation
C[N+]1([O-])CC[O:5]CC1.Br[CH2:10][C:11]1[C:16]2[CH:17]=[CH:18][O:19][C:15]=2[C:14]([F:20])=[CH:13][CH:12]=1>C(#N)C>[F:20][C:14]1[CH:13]=[CH:12][C:11]([CH:10]=[O:5])=[C:16]2[C:15]=1[O:19][CH:18]=[CH:17]2

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 19611656HCID 19611656, compound

Product 1

HCID 19611665HCID 19611665, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of the N-methylmorpholine-N-oxide (22.24) in acetonitrile (250 ml) containing 3 Å molecular sieves (8.71 g) was stirred at room temperature overnight, then cooled in ice. A solution of 4-bromomethyl-7-fluoro-benzofuran (23.45 g) in acetonitrile (50 ml) was added and the mixture stirred for 4 h. The mixture was filtered and the filtrate evaporated to dryness. Water and ether were added to the residue and the organic phase separated, washed with brine (2×200 ml), dried (MgSO4) and evaporated. The residue was triturated under ether (50 ml) and filtered to give the title compound as a pale yellow solid (5.45 g)

Workup

  1. temperaturecooled in ice
  2. stirringthe mixture stirred for 4 h
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. additionWater and ether were added to the residue
  6. customthe organic phase separated
  7. washwashed with brine (2×200 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was triturated under ether (50 ml)
  11. filtrationfiltered

Sources & evidence

ORD record
ord-1fedfcdf469c4d9b8eefc19f2695eeb7
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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