Ethyl ketone → HCID 86623760, compound

HRID 448096Notes

Reaction equation

HRID 448096 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][CH3:5].[CH3:7][C:8]([S:11]([NH2:13])=[O:12])([CH3:10])[CH3:9]>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:7][C:8]([S:11]([N:13]=[C:3]([CH2:4][CH3:5])[CH2:2][CH3:1])=[O:12])([CH3:10])[CH3:9]

Participants

6

Reactant 2

HCID 7288Ethyl ketoneHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 86623760HCID 86623760, compound

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a 40 mL vial, pentan-3-one (1.049 ml, 9.90 mmol) was dissolved in THF (17 ml). Titanium ethoxide (3.42 ml, 16.50 mmol) was added followed by addition of 2-methylpropane-2-sulfinamide (1.0 g, 8.25 mmol) and the reaction was heated to 90° C. for 36 hr. The reaction was poured into equal volume of brine and stirred for 30 min before filtration through a silica gel pad. The filtrate was dried with sodium sulfate, concentrated and purified over silica gel (hexane-EtOAc 4:1 as eluent) to provide title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.00 (m, 3 H) 1.06-1.13 (m, 3 H) 1.14 (s, 9 H) 2.50 (m, 2 H) 2.62 (m, 2 H). MS (DCI) m/z 190 (M+H)+.

Workup

  1. dry with materialThe filtrate was dried with sodium sulfate
  2. concentrationconcentrated
  3. custompurified over silica gel (hexane-EtOAc 4:1 as eluent)

Sources & evidence

ORD record
ord-0078ceb303a94a01924da54637e87111
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

Loading…