Water → (NE,S)-2-methyl-N-[1-(3-propan-2-ylphenyl)ethylidene]propane-2-sulfinamide

HRID 626395Notes

Reaction equation

HRID 626395 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:10](=O)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].O>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH:1]([C:4]1[CH:5]=[C:6](/[C:10](=[N:19]/[S@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])/[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 30854921-[3-(Propan-2-yl)phenyl]ethan-1-oneHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 90373684(NE,S)-2-methyl-N-[1-(3-propan-2-ylphenyl)ethylidene]propane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of 1-(3-isopropylphenyl)ethanone (5.8 g, 0.036 mol), (S)-2-methylpropane-2-sulfinamide (5.2 g, 0.043 mol) and Ti(OiPr)4 in THF was stirred at 90° C. for 16 hours. Then the mixture was poured to water and the solid was filtered, the filtrate was partitioned between EtOAc and water. The layers were separated and the organic layer was washed with water, brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography to give the titled compound.

Workup

  1. filtrationthe solid was filtered
  2. customthe filtrate was partitioned between EtOAc and water
  3. customThe layers were separated
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4aec13a538694f578ad3705545c44689
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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