3-Methylacetophenone → HCID 117761924, compound

HRID 709429Notes

Reaction equation

HRID 709429 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C1COCC1>[CH3:11][C:12]([S@:15](/[N:17]=[C:8](/[C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=1)\[CH3:9])=[O:16])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 114553-MethylacetophenoneHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 117761924HCID 117761924, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-(3-methylphenyl)ethanone (1.61 g, 12.0 mmol, 1.00 equiv.) and (R)-(+)-2-methyl-2-propanesulfinamide (1.94 g, 14 mmol, 1.33 equiv.) in THF (50 mL) was added Ti(OEt)4 (3.19 g, 14 mmol, 1.17 equiv.) dropwise. The reaction mixture was stirred for 16 h at 60° C., cooled to room temperature, and quenched with a saturated aqueous NaHCO3 solution (50 mL). The layers were separated and the aqueous layer was further extracted with EtOAc (2×100 mL). The combined organics were concentrated and the resulting residue was purified by flash chromatography (silica gel, eluting with 0-5% CH3OH in CH2Cl2) to afford 1.51 g (53%) of the title compound as a white solid. LC/MS: m/z (ES+) 238 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with a saturated aqueous NaHCO3 solution (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was further extracted with EtOAc (2×100 mL)
  5. concentrationThe combined organics were concentrated
  6. customthe resulting residue was purified by flash chromatography (silica gel, eluting with 0-5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-7959c80b3f74462c8edfdd05ac060c2b
Source dataset
uspto-grants-2015_11
Patent number
US09181200B2

Reaction notes

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