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

HRID 1840764

반응식

HRID 1840764 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 178418486HCID 178418486, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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 9, 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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-3e58a874c8644d30b22fc306466b38bc
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683087B2

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