Propargyl alcohol → Prop-2-ynyl 3-oxopentanoate

HRID 1471328노트

반응식

HRID 1471328 반응식
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:10](O)[C:11]#C>C1(C)C=CC=CC=1.II>[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH2:7][C:10]#[CH:11])=[O:5]

참가 물질

5

반응물 2

HCID 7859Propargyl alcoholHCID 121699Methyl 3-oxovalerate

생성물 1

HCID 58512883Prop-2-ynyl 3-oxopentanoate수율 43.4%

시약·촉매·용매 2

HCID 807Iodine촉매HCID 1140Toluene용매

반응 조건

온도
115 °C

실험 절차

To a solution of methyl 3-ketopentanoate (3) (822 mg, 6.00 mmol) and 2-propynol (686 mg, 12.0 mmol) in toluene (7 mL) is added I2 (46 mg, 0.18 mmol). The mixture is stirred at 115° C. for 6 h, then cooled to room temperature, and extracted with ethyl acetate (100 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is distilled (125-130° C., 2 mm) to give 401 mg (43%) of 4 as a colorless liquid. IR 3345, 2856, 1715, 1456 cm−1; 1H NMR (CDCl3) δ 1.10 (t, J=7.5 Hz, 3H, CH2CH3), 2.52 (t, J=2.4 Hz, 1H, CH≡CCH2), 2.58 (q, J=7.5 Hz, 2H, CH2CH3) 3.51 (s, 2H, CH2), 4.74 (d, J=2.4 Hz, 2H, CH≡CCH2).

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe extract is washed (brine)
  4. customdried
  5. customAfter solvent removal at reduced pressure
  6. distillationthe residue is distilled (125-130° C., 2 mm)

출처 및 근거

ORD 기록
ord-bcae3fa0d79f490eb7d2bc8b3b520f5b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012217B2

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