Nitroethane → HCID 419520, compound

HRID 929940Notes

Reaction equation

HRID 929940 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N+:7]([CH2:10][CH3:11])([O-:9])=[O:8].[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1>C1COCC1>[N+:7]([CH:10]([CH3:11])[CH:12]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[OH:19])([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 103713-PyridinecarboxaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 419520HCID 419520, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiAlH4 (2M in THF) (1.4 mL, 2.8 mmol) in dry THF (110 mL) at 0° C., was slowly added 1-nitroethane (2.00 mL, 28 mmol) under argon. After 20 min at 0° C., nicotinaldehyde (2.64 mL, 28 mmol) was added in one portion. The mixture was stirred for 16 hours, while allowing the temperature to rise from 0° C. to room temperature. The reaction mixture was quenched by addition of 5 mL of 1M HCl, followed by addition of CH2Cl2 and Na2SO4. The resulting suspension was stirred for 15 minutes and then filtered. The filtrate was concentrated. The residue was then purified by column chromatography (40 g of SiO2) using EtOAc in hexane from 0% to 100% in order to give the product as an oil (3.2 g, 63%) as a mixture of diastereoisomers. LC-MS: [M+H] 183.4; Rt 0.41 min; (LCMS method 1). A) 1H NMR (400 MHz, CHCl3-d): 8.58-8.48 (m, 2H), 7.68 (d, 1H) 7.33-7.23 (m, 1H) 5.42-5.38 (m, 1H), 4.70-4.60 (m, 1H), 3.30-2.90 (brs, 1H), 1.46 (d, B) 1H NMR (400 MHz, CHCl3-d): 8.58-8.48 (m, 2H), 7.68 (d, 1H) 7.33-7.23 (m, 1H) 5.04 (d, 1H), 4.76-4.69 (m, 1H), 3.30-2.90 (brs, 1H), 1.31 (d, 3H).

Workup

  1. customat 0° C.
  2. customto rise from 0° C. to room temperature
  3. customThe reaction mixture was quenched by addition of 5 mL of 1M HCl
  4. additionfollowed by addition of CH2Cl2 and Na2SO4
  5. stirringThe resulting suspension was stirred for 15 minutes
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe residue was then purified by column chromatography (40 g of SiO2)

Sources & evidence

ORD record
ord-7b3153a37b3c4cbdbe39f9da55dba980
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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