Water → 1-((2-Methoxyethoxy)methoxy)-4-((trans)-2-nitrocyclopropyl)benzene

Trimethylsulfoxonium iodide (0.76 g, 3.44 mmol) was added in small portions to a suspension of NaH 0.14 g (60% in mineral oil), 3.44 mmol] in dry DMSO (5 mL). The mixture was stirred until gas evolution ceased and a clear solution was formed (45 min). Then, a solution of (E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene (Intermediate J, 0.73 g, 2.86 mmol) in DMSO (5 mL) was transferred via cannula and the reaction was stirred for additional 20 h. The mixture was poured into water (20 mL) and extracted with Et2O (3×15 mL). The organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered; after removal of the solvent, the residual orange oil was purified by column chromatography on silica gel (10-20% EtOAc/Hexanes) affording 0.44 g of 1-((2-methoxyethoxy)methoxy)-4-((trans)-2-nitrocyclopropyl)benzene [Rf=0.4 (50% AcOEt/Hexanes), colorless oil, 36% yield].

1. customa clear solution was formed (45 min)
2. stirringthe reaction was stirred for additional 20 h
3. extractionextracted with Et2O (3×15 mL)
4. washThe organic layers were washed with brine (20 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customafter removal of the solvent
8. customthe residual orange oil was purified by column chromatography on silica gel (10-20% EtOAc/Hexanes)

ORD record

ord-46015b10b8a74124ac0fbccc7a9c2c12

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149447B2