Diethyl Malonate → Diethyl 2-pent-4-enylpropanedioate

HRID 1012948

반응식

HRID 1012948 반응식
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]>CN(C=O)C>[CH2:12]([O:11][C:3](=[O:10])[CH:4]([CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-

생성물 1

HCID 361718Diethyl 2-pent-4-enylpropanedioate수율 101.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

A mixture of sodium hydride (60% in mineral oil, 2.4 g, 60.5 mmol, 1.1 eq) and diethyl malonate (8.34 mL, 55 mmol, 1 eq) in DMF (200 mL) was cooled to 0° C. and 5-bromo-1-pentene (6.5 mL, 55 mmol, 1 eq) was added dropwise. The reaction mixture was warmed to rt, stirred for 14 hours and then partitioned between ether and water. The layers were separated, the aqueous layer was extracted with ether (2×250 mL) and the combined organic phases were washed with water (2×) and brine, dried over MgSO4 and concentrated to give E1.1 as a colorless oil (12.7 g, 100% yield). 1H NMR (400 MHz, CDCl3): δ 5.71 (m, 1H), 4.92 (m, 2H), 4.12 (q, J=7.1 Hz, 4H), 3.25 (t, J=7.58 Hz, 1H), 2.01 (m, 2H), 1.83 (m, 2H), 1.36 (m, 2H), 1.20 (t, J=7.1 Hz, 6H).

후처리

  1. temperatureThe reaction mixture was warmed to rt
  2. custompartitioned between ether and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (2×250 mL)
  5. washthe combined organic phases were washed with water (2×) and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-148b832ef6b6426f8d5ba32f2b579e31
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981881B2

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