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

HRID 491403ノート

反応式

HRID 491403 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9400ccdb69da490ba630e83494046cda
出典データセット
uspto-grants-2009_05
特許番号
US07531533B2

反応ノート

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