Acetone → HCID 58929043, compound

HRID 1888006Notes

Reaction equation

HRID 1888006 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH3:8][C:9]([CH3:11])=O>C1COCC1>[C:9](=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])([CH3:11])[CH3:8]

Participants

4

Reactant 2

HCID 180AcetoneHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 58929043HCID 58929043, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-Methyl-2-propanesulfinamide (1.47 g) and acetone (0.98 ml) in THF (24 ml) chilled to 0° C. was added Ti(OEt)4 (5.36 ml) dropwise over the course of 15 minutes. After being stirred at room temperature for 3 days, the reaction mixture was quenched by the rapid addition into ice cooled saturated sodium bicarbonate solution. The suspension was filtered through glass fiber filter paper, washing with ethyl acetate. The filtrate was washed with saturated sodium bicarbonate solution and brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (10-60% ethyl acetate in hexanes) gave the product (0.923 g, 47%). 400 M Hz 1H-NMR (CDCl3) δ: 2.34 (s, 3H), 2.18 (s, 3H), 1.23 (s, 9H).

Workup

  1. customthe reaction mixture was quenched by the rapid addition into ice cooled saturated sodium bicarbonate solution
  2. filtrationThe suspension was filtered through glass fiber
  3. filtrationfilter paper
  4. washwashing with ethyl acetate
  5. washThe filtrate was washed with saturated sodium bicarbonate solution and brine
  6. dry with materialThe organics were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (10-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2984c3313cbd43d0a9c7b398bb6385eb
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

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