HCID 15612083, compound → HCID 14442084, compound

HRID 580355Notes

Reaction equation

HRID 580355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=2)(=O)=[O:9])=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:19]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15612083HCID 15612083, compoundHCID 131709961Jones' reagent

Product 1

HCID 14442084HCID 14442084, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 0° C. solution of Example 8 Part A sulfide (500 mg, 1.11 mmol) in acetone (6 ml) was added, dropwise, freshly prepared Jones reagent (2.67M, ca. 1.2 ml). After stirring for 40 minutes, the reaction was quenched with 2-propanol and then concentrated in vacuo. The residue was then stirred with water (50 ml) for 30 minutes at which time a yellow solid had formed. The solid was collected by filtration, washed with water and air dried. Chromatography (flash, silica, 25 mm dia., ethyl acetate then 20% methanol/chloroform) provided a white solid. The solid was then triturated with 2 portions of hot ethyl acetate (ca. 10 ml each) leaving the desired sulfoxide as white amorphous solid: 1H NMR (tetradeuteriomethanol, 270 MHz) δ 7.53-7.62 (m, 4H), 7.02-7.19 (m, 4H), 3.46 (s, 2H), 2.55-2.95 (m, 4H), 1.75-2.00 (m, 2H); 13C NMR (tetradeuteriomethanol), 67.88 MHz, complete decoupling) δ 178.3, 142.4, 139.9, 138.3, 134.9, 130.6, 130.5, 129.4, 127.0, 56.4, 43.1.

Workup

  1. customthe reaction was quenched with 2-propanol
  2. concentrationconcentrated in vacuo
  3. stirringThe residue was then stirred with water (50 ml) for 30 minutes at which time a yellow solid
  4. customhad formed
  5. filtrationThe solid was collected by filtration
  6. washwashed with water and air
  7. customdried
  8. custom, ethyl acetate then 20% methanol/chloroform) provided a white solid
  9. customThe solid was then triturated with 2 portions of hot ethyl acetate (ca. 10 ml each)

Sources & evidence

ORD record
ord-3f2e259345fe485fac4db0620345b09f
Source dataset
uspto-grants-1988_06
Patent number
US04752616

Reaction notes

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