Methanol → HCID 14430179, 화합물

HRID 1731650노트

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HRID 1731650 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH2:3]1.[CH3:13]O>S(=O)(=O)(O)O>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:4]=[CH:3]1

참가 물질

4

반응물 2

HCID 887MethanolHCID 202283473-(4-Oxocyclohex-1-en-1-yl)propanoic acid

생성물 1

HCID 14430179HCID 14430179, 화합물

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

A solution of 3.5 g of 4-oxocyclohex-1-enepropionic acid in 16.5 ml of methanol and 0.9 ml of concentrated sulfuric acid was refluxed for 30 minutes. The mixture was cooled and the solvent was evaporated under reduced pressure. The resulting residue was partitioned between 50 ml of 5% aqueous sodium bicarbonate and 100 ml of ether. The separated aqueous layer was washed twice with 100-ml portions of ether and the washings were combined with the original organic layer and dried over magnesium sulfate. The solvent was evaporated to give a crude product which was found to be a 1:1 mixture of double bond isomers by NMR analysis. Flash chromatography of this crude product (silica gel, 3:7 ethyl acetate-hexane) separated the compounds and gave methyl 4-oxocyclohex-2-enepropionate as a clear oil. 1H NMR (CDCl3) δ 3.60 (s, 3H); 5.70-6.00 (dd, 1H); 6.60-6.95 (d of m, 1H).

후처리

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was partitioned between 50 ml of 5% aqueous sodium bicarbonate and 100 ml of ether
  4. washThe separated aqueous layer was washed twice with 100-ml portions of ether
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a crude product which
  8. additiona 1:1 mixture of double bond isomers by NMR analysis
  9. customFlash chromatography of this crude product (silica gel, 3:7 ethyl acetate-hexane) separated the compounds

출처 및 근거

ORD 기록
ord-34fc586212934e0aae4dae348d8443d5
출처 데이터셋
uspto-grants-1986_11
특허 번호
US04622422

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