Triphenylphosphine → Methyl 4-bromo-5-methylfuran-2-carboxylate

HRID 1257436

反応式

HRID 1257436 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1Br.[C:12]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Zn]Cl.[Cl-].[NH4+]>Cl[Pd]Cl.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1[CH3:12]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178477798HCID 178477798、化合物

生成物 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylate収率 1,830.4%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of the compound (1.80 g) obtained in Example 128a, palladium chloride(II) (0.02 g), triphenylphosphine (0.07 g) and tetrahydrofuran (30 mL) was added MeZnCl (2M tetrahydrofuran solution, 9.5 ml), and the mixture was heated under reflux for 4 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane ethyl acetate) to give the title compound (1.07 g) as a colorless solid.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr under a nitrogen atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane ethyl acetate)

出典と根拠

ORDレコード
ord-5f3bca02527d470a924e211a0b5035a5
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

関連ノート

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