Sulfuric Acid → 4-(3-Fluorophenyl)butanoic acid

HRID 13688ノート

反応式

HRID 13688 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O>[Pd].O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 537648234-(3-Fluoro-phenyl)-but-3-enoic acid

生成物 1

HCID 149151134-(3-Fluorophenyl)butanoic acid収率 101.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Hydrogenate a mixture of 4-(3-fluoro-phenyl)-but-3-enoic acid (22 g, 122 mmol), concentrated sulfuric acid (24 ml), and 5% palladium on carbon (3.58 g) in tetrahydrofuran (470 ml) at 60 psi at room temperature overnight. After filtration of the catalyst, remove most of the tetrahydrofuran by rotary evaporation, dilute the residue with ether, wash with water (2×), dry over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (22.50 g, 100%). NMR (400 MHz, CDCl3): δ 1.98 (m, 2H), 2.38 (t, 2H), 2.65 (t, 2H), 6.88 (m, 2H), 6.96 (d, 1H), 7.23 (m, 1H).

後処理

  1. filtrationAfter filtration of the catalyst
  2. customremove most of the tetrahydrofuran by rotary evaporation
  3. additiondilute the residue with ether
  4. washwash with water (2×)
  5. dry with materialdry over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

出典と根拠

ORDレコード
ord-daa45542a9834ddab492c34d5204fee0
出典データセット
uspto-grants-2010_06
特許番号
US07728150B2

反応ノート

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