Ethyl bromoacetate → Ethyl 3-acetyl-4-oxopentanoate

HRID 220456

반응식

HRID 220456 반응식
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[H-].[Na+].[CH2:10]([O:12][C:13](=[O:16])[CH2:14]Br)[CH3:11]>O1CCCC1>[CH2:10]([O:12][C:13](=[O:16])[CH2:14][CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])[CH3:11]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 31261Acetylacetone

생성물 1

HCID 87820Ethyl 3-acetyl-4-oxopentanoate수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Add pentane-2,4-dione (2.0 g, 20.6 mmol) in tetrahydrofuran (30 mL) to a chilled (0° C.) suspension of 60% sodium hydride (0.99 g, 24.7 mmol) in tetrahydrofuran (40 mL). Stir for 1 hr. Then add bromoacetic acid ethyl ester (2.73 mL, 24.7 mmol) in tetrahydrofuran (30 mL) dropwise. Stir at 0° C. to room temperature for 16 hr. Partition between diethyl ether (100 mL) and saturated aqueous ammonium chloride solution (50 mL). Separate organic layer, dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 9:1 hexanes:ethyl acetate), to give 3-acetyl-4-oxopentanoic acid ethyl ester (3.34 g, 94%). 1H NMR (CDCl3) δ 5.15 (q, 2H), 5.1 (t, 1H), 2.84 (d, 2H), 2.23 (s, 6H), 1.22 (t, 3H).

후처리

  1. temperaturea chilled
  2. stirringStir at 0° C. to room temperature for 16 hr
  3. customPartition between diethyl ether (100 mL) and saturated aqueous ammonium chloride solution (50 mL)
  4. dry with materialSeparate organic layer, dry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 9:1 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-470d29832e0b4449b6e113eba46b2f63
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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