Hydrochloric Acid → 5-(1-Hydroxy-2-methylprop-2-enyl)furan-2-carboxylic acid benzyl ester

HRID 332610

反応式

HRID 332610 の反応式
[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([Mg]Br)[CH:19]=[CH2:20].Cl>O1CCCC1>[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([CH:16]([OH:17])[C:19]([CH3:20])=[CH2:18])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 600347885-Formyl-2-furancarboxylic acid benzyl esterHCID 178455850HCID 178455850、化合物

生成物 1

HCID 866733225-(1-Hydroxy-2-methylprop-2-enyl)furan-2-carboxylic acid benzyl ester収率 94.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-Formyl-2-furancarboxylic acid benzyl ester (300 mg, 1.30 mmol) was dissolved in tetrahydrofuran (12 mL), 2-propenylmagnesium bromide (0.5 mol/L tetrahydrofuran solution, 2.6 mL, 1.3 mmol) was added at −78° C., and the mixture was stirred for 15 minutes. 1N Hydrochloric acid was added to the reaction mixture, the mixture was heated to room temperature and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30) to give the title compound (332 mg, 1.23 mmol, 94%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30)

出典と根拠

ORDレコード
ord-6bb6b5833c3f4160919148895af1c4d5
出典データセット
uspto-grants-2014_11
特許番号
US08877805B2

関連ノート

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