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

HRID 642234노트

반응식

HRID 642234 반응식
[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]

참가 물질

5

반응물 2

HCID 7626Beta-NitrostyreneHCID 87089461Ethyl acetoacetatesodium salt

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e1e9f56439fd43769bd03faf86755bbd
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

반응 노트

불러오는 중…