Beta-Nitrostyrene → Ethyl 2-acetyl-4-nitro-3-phenylbutanoate

HRID 642234Notes

Reaction equation

HRID 642234 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[Na].[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>CCOCC.CCOC(C)=O>[CH2:20]([O:19][C:13](=[O:18])[CH:14]([C:15](=[O:16])[CH3:17])[CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][N+:1]([O-:3])=[O:2])[CH3:21]

Participants

5

Reactant 2

HCID 7626Beta-NitrostyreneHCID 87089461Ethyl acetoacetatesodium salt

Product 1

HCID 11323434Ethyl 2-acetyl-4-nitro-3-phenylbutanoateYield 106.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-nitro-vinyl)-benzene (2.135 g, 14.3 mmol) in ether (30 mL) at 0° C. was added ethyl acetoacetate sodium salt (2.29 g, 14.3 mmol) portionwise in half minute; after addition, the mixture was stirred at that temperature for 1 hour; then it was diluted with EtOAc, washed with diluted hydrochloride aqueous solution and saturated sodium chloride aqueous solution respectively, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, oil-pumped to dryness to give a brown oil, the crude titled product (4.266 g); 1H NMR (200 MHz, CDCl3): δ (ppm)=7.4-7.2 (m, 5H), 4.73 (d, 1H, J=5.9 Hz), 4.2-3.9 (m, 4H), 2.30 (s, 3H), 1.01 (m, 3H).

Workup

  1. additionafter addition
  2. washwashed with diluted hydrochloride aqueous solution and saturated sodium chloride aqueous solution respectively
  3. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customoil-pumped to dryness to give a brown oil

Sources & evidence

ORD record
ord-e1e9f56439fd43769bd03faf86755bbd
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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