Dinitrobenzonitrile → HCID 66745849, compound

HRID 471651Notes

Reaction equation

HRID 471651 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[Li]CCCC.[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([N+]([O-])=O)[C:18]=1[C:19]#[N:20])([O-:16])=[O:15]>C1COCC1.CCCCCC>[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([O:8][CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[C:18]=1[C:19]#[N:20])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 520718DinitrobenzonitrileHCID 2773573(Oxan-4-yl)methanolHCID 178418339Butyllithium

Product 1

HCID 66745849HCID 66745849, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of tetrahydropyran-4-methanol (782 mg, 6.73 mmol) in THF (25 mL), was added slowly 1.38M nBuLi (4.13 mL, 5.70 mmol) in hexane at −78° C. under nitrogen. At one hour a solution of 2,6-dinitrobenzonitrile (1.00 g, 5.18 mmol) in THF (25 mL) was added. The reaction was stirred under N2 overnight at rt, then was quenched with water (100 mL). The precipitate was collected by filtration to provide 2-nitro-6-((tetrahydro-2H-pyran-4-yl)methoxy)benzonitrile (1.13 g, 83%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ 1.68 (m, 2H), 2.06 (br, 1H), 3.33 (m, 2H), 3.88 (m, 2H), 4.11 (d, J=6.0 Hz, 2H), 7.72 (d, J=6.0 Hz, 1H), 7.89-7.85 (m, 2H).

Workup

  1. customwas quenched with water (100 mL)
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8e846e88adcf4de2979c5465bafba585
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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