Tetrahydrofuran → 2-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

HRID 624272

Reaction equation

HRID 624272 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[CH2:12][CH2:11][CH2:10]C1.O1CC(=O)C1>[Cl-].[Na+].O.C(O[Ti](OCC)(OCC)OCC)C>[CH3:1][C:2]([S:5]([N:7]=[C:11]1[CH2:10][O:8][CH2:12]1)=[O:6])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 3382465Tert-ButanesulfinamideHCID 150242543-Oxetanone

Product 1

HCID 468399952-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a 250 mL round-bottomed flask was added 2-methylpropane-2-sulfinamide (3.36 g, 27.8 mmol) followed by tetraethoxytitanium (11.64 ml, 55.5 mmol) to a tetrahydrofuran (69.4 ml) solution of oxetan-3-one (2 g, 27.8 mmol) at room temperature. The mixture was stirred at 50° C. for 5 hours, cooled and poured into brine. The suspension was filtered through a pad of diatomaceous earth eluting with ethyl acetate. The organics were combined, dried with sodium sulfate, filtered and concentrated under vacuum. The residue was purified by regular phase flash column chromatography to give the title compound.

Workup

  1. temperaturecooled
  2. filtrationThe suspension was filtered through a pad of diatomaceous earth
  3. washeluting with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by regular phase flash column chromatography

Sources & evidence

ORD record
ord-3d453ee755554741a9d6bc4cb6c12527
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Linked notes

Loading…