Water → N-(4-Hydroxycyclopent-2-enyl)-benzamide

HRID 351364

Reaktionsgleichung

Reaktionsgleichung von HRID 351364
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[N:3]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])[O:2]2.C(#N)C.O.[BH4-].[Na+]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C(OCC)(=O)C>[OH:2][CH:1]1[CH2:7][CH:4]([NH:3][C:8](=[O:9])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6342AcetonitrileHCID 328016(2-Oxa-3-azabicyclo[2.2.1]hept-5-en-3-yl)-phenylmethanoneHCID 4311764Sodium borohydride

Produkt 1

HCID 12498570N-(4-Hydroxycyclopent-2-enyl)-benzamideAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)KatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Molybdenum hexacarbonyl (12.1 g, 45.8 mmol) was added to a solution of the bicycle 7 (6.10 g, 30.3 mmol) in a 7:1 mixture of acetonitrile and water (280 cm3). The suspension was stirred for 30 minutes at room temperature, then sodium borohydride (0.60 g, 15.9 mmol) was added and the suspension was heated under reflux for 4 hours. Upon completion of reaction, the mixture was allowed to cool to room temperature, filtered though a celite plug, and evaporated to dryness to give a brown solid. Flash chromatography (SiO2, 80% ethyl acetate in petrol) gave the alcohol 8 (3.60 g, 17.7 mmol, 58%) as a light yellow solid; m/z (EI) Found [M]+ 203.0945 ([M]+ C12H13NO2 requires 203.0946).

Aufarbeitung

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 4 hours
  3. customUpon completion of reaction
  4. temperatureto cool to room temperature
  5. filtrationfiltered though a celite plug
  6. customevaporated to dryness
  7. customto give a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-e996446102ae44f3a39642c31abc9e92
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183440B2

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