Propargyl alcohol → Prop-2-ynyl 3-oxopentanoate

HRID 1471328ノート

反応式

HRID 1471328 の反応式
[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]

参加物

5

反応物 2

HCID 7859Propargyl alcoholHCID 121699Methyl 3-oxovalerate

生成物 1

HCID 58512883Prop-2-ynyl 3-oxopentanoate収率 43.4%

試薬・触媒・溶媒 2

HCID 807Iodine触媒HCID 1140Toluene溶媒

反応条件

温度
115 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bcae3fa0d79f490eb7d2bc8b3b520f5b
出典データセット
uspto-grants-2015_04
特許番号
US09012217B2

反応ノート

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