1,4-Dioxane → HCID 68465189, compound

HRID 1700266Notes

Reaction equation

HRID 1700266 reaction equation
C[N:2]1[CH:7]=[CH:6][C:5](C2C=CC(C)=CC=2)=[CH2+:4][CH:3]1[O-].C([S@](C1C=CC(C)=CC=1)=O)=C.[O:27]1[CH2:32][CH2:31]OCC1>>[CH:3]12[NH:2][CH:7]([CH2:5][CH2:4]1)[CH:6]=[CH:31][C:32]2=[O:27]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 11105722(+)-(R)-p-tolyl vinyl sulphoxide

Product 1

HCID 68465189HCID 68465189, compound

Procedure

A solution of 1-methyl-4-(p-tolyl)-3-pyridiniumolate 26 (1.86 g, 8.37 mmol) and (+)-(R)-p-tolyl vinyl sulphoxide (1.07 g, 6.45 mmol) in dioxane (50 mL) was allowed to reflux for 20 hours. The resulting reaction mixture was concentrated under reduced pressure, purified by silica gel flash chromatography, and recrystallized from EtOAc to give the compound 29 as a white solid: [α]25D −47° (c 0.8, CH2Cl2); Rf0.6 (EtOAc); mp 188° C.

Workup

  1. temperatureto reflux for 20 hours
  2. customThe resulting reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. custompurified by silica gel flash chromatography
  5. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-d350cffd0a29409ca3d054e1ccdf81e9
Source dataset
uspto-grants-2002_02
Patent number
US06350758B1

Reaction notes

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