Nitromethane → HCID 58718575, compound

HRID 897173Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:13])[CH:5]=[C:6]1[CH2:10][C@@H:9]([CH3:11])[C@H:8]([CH3:12])[CH2:7]1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[N+:32]([CH3:35])([O-:34])=[O:33]>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1([CH2:35][N+:32]([O-:34])=[O:33])[CH2:7][C@@H:8]([CH3:12])[C@H:9]([CH3:11])[CH2:10]1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (2) (4.24 g, 23.3 mmol) in THF (15 mL) was added TBAF (32 mL of a 1 M solution in THF, 32 mmol) followed by nitromethane (3 mL) and the reaction heated at 60° C. for 8 hours. After cooling, the reaction mixture was diluted with ethyl acetate (150 mL) and washed with 2N HCl (40 mL) then saturated brine (50 mL). Column chromatography (10:1 heptane/ethyl acetate) gave the product as an oil, 2.24 g, 40%.

Workup

temperatureAfter cooling
washwashed with 2N HCl (40 mL)

Sources & evidence

ORD record: ord-cdfd1f60f02e4468b97cca3585324634
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921835B2

Reaction notes

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