Tetrabutylammonium Fluoride → Imino(4-methoxyphenyl)methyl-lambda6-sulfanone

HRID 1099605

Reaction equation

HRID 1099605 reaction equation
[CH3:1][S:2]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[N:4]S(CC[Si](C)(C)C)(=O)=O)=[O:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([S:2]([CH3:1])(=[NH:4])=[O:3])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57657885HCID 57657885, compound

Product 1

HCID 12463931Imino(4-methoxyphenyl)methyl-lambda6-sulfanoneYield 96%

Conditions

Temperature
120 °C

Procedure

A mixture of S-methyl-S-(4-methoxyphenyl)-N-[[2-(trimethylsilyl)ethyl]sulfonyl]-sulfoximine (2.9 g, 8.3 mmol) and 1.0 M of TBAF (12.5 mL, 12.5 mmol, 1.5 eq.) was heated in a microwave at 120° C. for 20 minutes. After cooling to room temperature, the solvent was evaporated and the resulting mixture was purified by silica gel column chromatography (elution with 100% EtOAc) to provide the title compound (1.46 g, yield 96%). 1H NMR (300 MHz, CDCl3) δ 7.92 (d, J=9.0 Hz, 2H), 6.99 (d, J=9 Hz, 2H), 3.87 (s, 3H), 3.08 (s, 3H); ESI-MS m/z 186.1 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated
  3. customthe resulting mixture was purified by silica gel column chromatography (elution with 100% EtOAc)

Sources & evidence

ORD record
ord-b7517dd9796e4296a66e8e82eec10616
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Linked notes

Loading…