2-Azetidinone → HCID 21940668, compound

HRID 2179134Notes

Reaction equation

[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].I[C:7]1[CH:8]=[C:9]([CH3:14])[CH:10]=[C:11]([CH3:13])[CH:12]=1>>[CH3:14][C:9]1[CH:8]=[C:7]([N:1]2[CH2:4][CH2:3][C:2]2=[O:5])[CH:12]=[C:11]([CH3:13])[CH:10]=1

Participants

Reactant 2

HCID 1367212-Azetidinone

HCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 21940668HCID 21940668, compoundYield 95%

Procedure

Using general procedure A, 2-azetidinone (88 mg, 1.24 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 1:1; 15 mL fractions). Fractions 5-10 provided 173 mg (95% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.01 (s, 2H), 6.76 (s, 1H), 3.61 (t, J=4.5 Hz, 2H), 3.10 (t, J=4.5 Hz, 2H), 2.32 (s, 6H).

Workup

customThe crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 1:1; 15 mL fractions)

Sources & evidence

ORD record: ord-ecb399cf306b4823b062f0940abdfe97
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067955B2

Reaction notes

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