Ethyl bromoacetate → Ethyl 4-oxo-3-propanoylhexanoate

HRID 220489

반응식

HRID 220489 반응식
[CH3:1][CH2:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[H-].[Na+].[CH2:12]([O:14][C:15](=[O:18])[CH2:16]Br)[CH3:13]>O1CCCC1>[CH2:12]([O:14][C:15](=[O:18])[CH2:16][CH:4]([C:3](=[O:9])[CH2:2][CH3:1])[C:5](=[O:8])[CH2:6][CH3:7])[CH3:13]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 819233,5-Heptanedione

생성물 1

HCID 50988004Ethyl 4-oxo-3-propanoylhexanoate수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Dissolve heptane-3,5-dione (2.5 g, 19.5 mmol) in dry tetrahydrofuran (10 mL) and add the resulting solution dropwise to a chilled (0° C.) suspension of sodium hydride (0.94 g, 23.4 mmol, 60% dispersion in oil) in tetrahydrofuran (20 mL). Stir at 0° C. for 1 hr., then add bromoacetic acid ethyl ester (2.6 mL, 23.4 mmol) dropwise. Stir for 16 hr. at 0° C. and warm to room temperature. Partition the reaction mixture between diethyl ether (100 mL) and saturated aqueous ammonium chloride solution (50 mL). Separate the organic layer and wash with saturated aqueous sodium chloride solution (50 mL), dry (sodium sulfate), filter and concentrate. Purify using silica gel chromatography, eluting with 10:1 hexanes:ethyl acetate, to give 4-oxo-3-propionyl-hexanoic acid ethyl ester as an oil (3.2 g, 77%). 1H-NMR (400 MHz, CDCl3) δ 4.08 (m, 3H), 2.83 (d, 2H), 2.55 (q, 2H), 1.21 (t, 3H), 1.02 (t, 6H).

후처리

  1. additionadd the resulting solution dropwise to
  2. temperaturea chilled
  3. stirringStir for 16 hr
  4. temperatureat 0° C. and warm to room temperature
  5. customPartition the reaction mixture between diethyl ether (100 mL) and saturated aqueous ammonium chloride solution (50 mL)
  6. customSeparate the organic layer
  7. washwash with saturated aqueous sodium chloride solution (50 mL)
  8. dry with materialdry (sodium sulfate)
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify
  12. washeluting with 10:1 hexanes

출처 및 근거

ORD 기록
ord-e5cf9ef8eeba4791a5c43d82a63ad79c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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