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

HRID 1383531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383531
[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)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of methyl 3-hydroxy-4-(methylthio)benzoate (1.98 g; that is prepared as described in Reference Example 53) in dry dimethyl-formamide (40 mL) is treated with sodium hydride (0.44 g of a 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. customthat is prepared
  2. stirringstirred at 60° C. for 3 hours
  3. concentrationconcentrated
  4. customThe resulting residue is partitioned between dichloromethane (50 mL) and water (50 mL)
  5. extractionthe aqueous layer is extracted with dichloromethane (50 mL)
  6. customthe combined organic layers are dried
  7. concentrationconcentrated
  8. customto give a red oil
  9. washeluting with a mixture of diethyl ether and pentane (1:9 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-d520f7babe904b18899c7a87a0cb8e86
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255326B1

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