Beta-Nitrostyrene → HCID 59200437, compound

HRID 1685314Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][CH2:10][O:11][CH3:12].C([Mg]Br)(C)C.[N+:18]([CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O-:20])=[O:19]>C1COCC1>[CH3:12][O:11][CH2:10][O:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][N+:18]([O-:20])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 1-iodo-2-((methoxymethoxy)methyl)benzene (4.51 g, 16.22 mmol) in THF (40 mL) under argon was added dropwise a solution of i-PrMgBr (9.5 mL, 2.12M in Et2O, 20.14 mmol) via syringe. The stirring was maintained at 0° C. After 1 hour, a solution of nitrostyrene (2.014 g, 13.50 mmol) in THF (40 mL) was added via cannula over 10 minutes and the stirring was maintained at 0° C. After 30 minutes, the reaction was quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined extracts were dried (MgSO4), filtered and concentrated to an oil which was purified on Biotage Horizon (10-50% EtOAc:hexane, SiO2, 40+M) to afford the product (2.93 g) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.35-7.39 (m, 1H), 7.27-7.34 (m, 3H), 7.22-7.27 (m, 5H), 5.34 (t, J=8.08 Hz, 1H), 4.94-5.03 (m, 2H), 4.73 (d, J=11.87 Hz, 1H), 4.68 (q, J=6.57 Hz, 2H), 4.57 (d, J=11.87 Hz, 1H), 3.42 (s, 3H).

Workup

temperaturethe stirring was maintained at 0° C
waitAfter 30 minutes
customthe reaction was quenched with saturated NH4Cl
extractionextracted with EtOAc (2×)
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated to an oil which
customwas purified on Biotage Horizon (10-50% EtOAc:hexane, SiO2, 40+M)

Sources & evidence

ORD record: ord-084f816cd93141be9361334c4dfd1722
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148400B2

Reaction notes

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