1,4-Dioxane → HCID 57016694, compound

HRID 1700267Notes

Reaction equation

HRID 1700267 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH2+:4][CH:3]1[O-].[CH:16]([S@:18]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[O:19])=[CH2:17].[O:27]1CCOCC1>>[CH3:1][N:2]1[C@@H:3]2[C@H:16]([S:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[O:19])[CH2:17][C@H:7]1[C:6](=[O:27])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[CH:4]2

Participants

3

Reactant 2

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

Product 1

HCID 57016694HCID 57016694, compound

Procedure

A solution of 1-methyl-4-(p-fluorophenyl)-3-pyridiniumolate 27 (2.45 g, 12.04 mmol) and (+)-(R)-p-tolyl vinyl sulphoxide (2.00 g, 12.04 mmol).in dioxane (25 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 30 as a white solid; [α]25D −77° (c 1.25, CHCl3); Rf0.2 (EtOAc/hexane, 7/3); mp 186° C. (EtOAc); 1H NMR (CDCl3) δ1.64 (dd, H7α, J=8.7 and 14.7 Hz), 2.14 (ddd, H7β, J=3.6, 7.8 and 14.7 Hz), 2.42 (s, 3H), 2.62 (s, 3H), 3.33 (dd, H6, J=3.6 and 8.7 Hz), 3.73 (d, H1, J=7.5 Hz), 4.51 (d, H5, J=5.4 Hz), 7.01 (d, H4, J=5.4 Hz), 7.041 (t, 2H, J=8.7 Hz), 7.30-7.40 (m, 4H), 7.66 (d, 2H, J=8.1 Hz).

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-69902c3937b345f78bdf13389fe8b002
Source dataset
uspto-grants-2002_02
Patent number
US06350758B1

Reaction notes

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