Bromocyclopentane → Methyl 3-cyclopentyloxy-4-(methylthio)benzoate

HRID 356920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356920
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[H-].[Na+].[CH:16]1(Br)[CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[CH:16]1([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=2[S:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

5

Edukt 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 21187893Methyl 3-hydroxy-4-(methylthio)benzoate

Produkt 1

HCID 21187944Methyl 3-cyclopentyloxy-4-(methylthio)benzoateAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of methyl 3-hydroxy-4(methylthio)benzoate (1.98 g) in dry dimethylformamide (40 mL) is treated with sodium hydride (0.44 g; 60% dispersion in mineral oil; 11 mmol) and the solution is stirred for a further 25 minutes. The reaction mixture is treated with cyclopentyl bromide (1.64 g), stirred at 60° C. for 3 hours, and then concentrated. The resulting residue is partitioned between dichloromethane (50 mL) and water (50 mL), the aqueous layer is extracted with dichloromethane (50 mL), and the combined organic layers are dried and concentrated, to give a red oil. The oil is subjected to flash chromatography, eluting with a mixture of diethyl ether and pentane (1:9 v/v), to give methyl 3-cyclopentyloxy-4-(methylthio)benzoate (1.9 g), m.p. 53°-55° C.

Aufarbeitung

  1. stirringstirred at 60° C. for 3 hours
  2. concentrationconcentrated
  3. customThe resulting residue is partitioned between dichloromethane (50 mL) and water (50 mL)
  4. extractionthe aqueous layer is extracted with dichloromethane (50 mL)
  5. customthe combined organic layers are dried
  6. concentrationconcentrated
  7. customto give a red oil
  8. washeluting with a mixture of diethyl ether and pentane (1:9 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-2e3d148708f54a80bf0ed09f11d0a97c
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840724

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