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

HRID 642234ノート

反応式

HRID 642234 の反応式
[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]

参加物

5

反応物 2

HCID 7626Beta-NitrostyreneHCID 87089461Ethyl acetoacetatesodium salt

生成物 1

HCID 11323434Ethyl 2-acetyl-4-nitro-3-phenylbutanoate収率 106.8%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e1e9f56439fd43769bd03faf86755bbd
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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