Methanol → N-[2-methyl-3(2-oxo-ethyl)-phenyl]-methanesulfonamide

HRID 618235Notes

Reaction equation

[C:1]([CH2:3][C:4]1[C:5]([CH3:15])=[C:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)#N.[H-].C([Al+]CC(C)C)C(C)C.C[OH:27]>O1CCCC1>[CH3:15][C:5]1[C:4]([CH2:3][CH:1]=[O:27])=[CH:9][CH:8]=[CH:7][C:6]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]

Participants

Conditions

Temperature: 5 °C

Procedure

N-(3-cyanomethyl-2-methyl-phenyl)-methanesulfonamide (3.75 g) was dissolved in 50 ml of dry tetrahydrofuran and cooled in an ice bath under an atmosphere of nitrogen. To this mixture was added 67 ml of 1M diisobutylaluminum hydride (DIBAL) in tetrahydrofuran. The mixture was stirred at 5° C. for 75 minutes. Excess reagent was decomposed with methanol and the solvent was evaporated. The residue was treated with EtOAc, washed with cold 1M hydrochloric acid, washed with brine and dried, and the solvent was evaporated. The residue was purified by silica gel chromatography eluting with methanol:dichloromethane (5:95), giving 1.1 g of N-[2-methyl-3(2-oxo-ethyl)-phenyl]-methanesulfonamide as a yellow oil.

Workup

temperaturecooled in an ice bath under an atmosphere of nitrogen
customthe solvent was evaporated
additionThe residue was treated with EtOAc
washwashed with cold 1M hydrochloric acid
washwashed with brine
customdried
customthe solvent was evaporated
customThe residue was purified by silica gel chromatography
washeluting with methanol:dichloromethane (5:95)

Sources & evidence

ORD record: ord-8b4f15751fb748c3952b89fe9c0187fe
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952362

Reaction notes

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