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

HRID 13688노트

반응식

HRID 13688 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 149151134-(3-Fluorophenyl)butanoic acid수율 101.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-daa45542a9834ddab492c34d5204fee0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728150B2

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