Nitromethane → HCID 13023786, compound

HRID 642252Notes

Reaction equation

HRID 642252 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[CH3:5][C:6]([CH3:10])([CH3:9])[CH:7]=[O:8].C(N(CC)CC)C>CCOC(C)=O>[CH3:5][C:6]([CH3:10])([CH3:9])[CH:7]([OH:8])[CH2:4][N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 12417Pivalaldehyde

Product 1

HCID 13023786HCID 13023786, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of nitromethane (5.87 g, 68.1 mmol), 2,2-dimethyl-propionaldehyde (5.4 g, 88.6 mmol), and triethylamine (689 mg, 6.8 mmol) was stirred at room temperature for two days; then the reaction mixture was diluted with EtOAc, washed with diluted HCl aqueous solution, and saturated NaCl aqueous solution respectively, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated to give a clear oil, the title product (7.35 g); The title product, 1H NMR (200 MHz, CDCl3): δ (ppm)=4.52 (dd, 1H, J=2.4 Hz, 12.6 Hz), 4.36 (dd, 1H, J=10.0 Hz, 12.6 Hz), 4.01 (m, 1H), 2.42 (d, 1H, J=4.4 Hz), 0.98 (s, 9H).

Workup

  1. washwashed with diluted HCl aqueous solution, and saturated NaCl aqueous solution respectively
  2. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a clear oil

Sources & evidence

ORD record
ord-553af7c975f344a99a4fb65e2c10f2a4
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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