Hydrochloric Acid → 3-Ethynylcyclohex-2-en-1-one

HRID 890595

反応式

HRID 890595 の反応式
[C:1]([Mg]Br)#[CH:2].C(O[C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=1)C.Cl>O1CCCC1>[C:1]([C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=1)#[CH:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 178418486HCID 178418486、化合物

生成物 1

HCID 145707953-Ethynylcyclohex-2-en-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 0.5N ethynylmagnesium bromide in tetrahydrofuran (100 mL) was added under N2 and stirring 3-ethoxy-2-cyclohexen-1-one (3.75 g, 26.8 mmol) in tetrahydrofuran (12.5 mL). The mixture was stirred at RT for 20 h when it was acidified with 1N HCl (200 mL). After stirring for 15 min the acidic phase was extracted with dichloromethane (5×50 mL). The combined organic extracts were washed with water (2×50 mL) and dried (MgSO4). Evaporation of the solvent gave an oil that was purified by column chromatography (silica, ethyl acetate/hexane 1:9) to yield a yellow oil, 2.71 g, 22.6 mmol, 84%). Analysis were in agreement with literature data.

後処理

  1. stirringAfter stirring for 15 min the acidic phase
  2. extractionwas extracted with dichloromethane (5×50 mL)
  3. washThe combined organic extracts were washed with water (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customgave an oil that
  7. customwas purified by column chromatography (silica, ethyl acetate/hexane 1:9)
  8. customto yield a yellow oil, 2.71 g, 22.6 mmol, 84%)

出典と根拠

ORDレコード
ord-2e11234de2b24e4ea1555866d926327e
出典データセット
uspto-grants-2006_02
特許番号
US06998405B2

関連ノート

読み込み中…