Ethyl Acetate → 3-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL

HRID 593363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593363
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([O:11]C(=O)C)[CH2:7][CH2:8][C:9]=2[CH:10]=1.[OH-].[Na+].CCCCCCC.C(OCC)(=O)C>CO.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([OH:11])[CH2:7][CH2:8][C:9]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 14798Sodium HydroxideHCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

Produkt 1

HCID 580828163-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OLAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of acetic acid 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl ester (1.57 g, 7.42 mmol) in methanol (35.7 ml) was treated with 1M sodium hydroxide (8.9 ml). The mixture was stirred at room temperature for 1.5 hours. The reaction was followed by TLC (silica gel, heptane: ethyl acetate=1:1; UV detection 254 nm). After completion, the reaction mixture was treated with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulphate, then evaporated leaving a dark red liquid (1.15 g, 91%) which crystallised on standing. Following NMR the product was pure enough for the next step of the synthesis; (calculated) C8H8ClNO [169.61]; (found) [M+H]+=170.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0fd45fee51bb4036abcab90002729c7a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242943B2

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