Hydrochloric Acid → Methyl 3-ethyl-1-benzofuran-2-carboxylate

HRID 2091017노트

반응식

HRID 2091017 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][CH3:10].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+].N12CCCN=C1CCCCC2.Cl>CN(C)C=O.CC(C)=O>[CH2:9]([C:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1][C:13]=1[C:14]([O:16][CH3:17])=[O:15])[CH3:10]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 691332'-HydroxypropiophenoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 66778182Methyl 3-ethyl-1-benzofuran-2-carboxylate수율 52%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 1-(2-hydroxyphenyl)propan-1-one (10.0 g), methyl bromoacetate (5.11 mL) and acetone (100 mL) was added potassium carbonate (18.4 g), and the mixture was stirred overnight at room temperature. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give a colorless oil. To a solution (150 mL) of the obtained oil in N,N-dimethylformamide was added 1,8-diazabicyclo[5.4.0]undec-7-ene (8.12 mL), and the mixture was stirred at 120° C. for 2 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. Ethyl acetate was added to the residue, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio) to give the title object compound (7.14 g, 52%) as a white solid.

후처리

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)
  4. customto give a colorless oil
  5. stirringthe mixture was stirred at 120° C. for 2 hr
  6. customto quench
  7. customthe reaction
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. additionEthyl acetate was added to the residue
  13. filtrationthe insoluble material was filtered off
  14. concentrationthe filtrate was concentrated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio)

출처 및 근거

ORD 기록
ord-d46a4e17ca2148adbe03cef3788ca2d0
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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