Water → Methyl 5-(3-oxopropyl)furan-2-carboxylate

HRID 491403노트

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HRID 491403 반응식
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].C(=O)([O-])O.[Na+].[CH2:16]([OH:19])[CH:17]=[CH2:18].O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH:16]([CH2:17][CH2:18][C:7]1[O:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][CH:8]=1)=[O:19]

참가 물질

9

반응물 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 599633Methyl 5-bromofuran-2-carboxylate

생성물 1

HCID 12412564Methyl 5-(3-oxopropyl)furan-2-carboxylate수율 28.1%

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A solution of 5-bromo-2-furancarboxylic acid methyl ester (816 mg, MAYB) in DMF (3 ml) was added with tetra-n-butylammonium chloride (1.1 g, TCI), sodium hydrogencarbonate (688 mg), palladium acetate (10.4 mg, WAKO), and allyl alcohol (346 mg, TCI), and the mixture was stirred at 60° C. for 20 hours. The reaction solution was added with distilled water (30 ml), and ethyl acetate (20 ml), and the insoluble solid was removed by filtration. The filtrate was extracted with ethyl acetate (50 ml×2). The organic layers were combined, washed with saturated brine, and dried, and then the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Flash, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate ih-01, 204 mg).

후처리

  1. customthe insoluble solid was removed by filtration
  2. extractionThe filtrate was extracted with ethyl acetate (50 ml×2)
  3. washwashed with saturated brine
  4. customdried
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (Flash, hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-9400ccdb69da490ba630e83494046cda
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531533B2

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