Sodium hydride → Methyl 3-(4-cyclopentylmethyloxyphenyl)propionate

HRID 2378524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378524
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(Cl)(=O)=O.[H-].[Na+].O[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1>O1CCCC1.CN(C)C=O.C(OCC)C.O.C(N(CC)CC)C>[CH:1]1([CH2:6][O:7][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

10

Edukt 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 77195CyclopentanemethanolHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Produkt 1

HCID 22559097Methyl 3-(4-cyclopentylmethyloxyphenyl)propionate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of cyclopentane methanol (4.05 ml, Ald) in anhydrous tetrahydrofuran (abbreviated as “THF” hereinafter, 40 ml) was added with triethylamine (6.49 ml, WAKO), added dropwise with methanesulfonyl chloride (3.48 ml, WAKO) under ice cooling, and stirred for 30 minutes. The reaction mixture was added with water (50 ml), and extracted with diethyl ether (80 ml×2). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. A solution obtained beforehand by adding 60% sodium hydride (1.15 g, KANTO) to a solution of Intermediate 1 (4.50 g) in N,N-dimethylformamide (abbreviated as “DMF” hereinafter, 35 ml) under ice cooling and stirring the solution for 15 minutes was added with a solution of the aforementioned residue in DMF (10 ml) under ice cooling. The reaction mixture was stirred for 15 minutes, then warmed to room temperature, stirred for 45 minutes, and further stirred at 60° C. for 15 hours. The reaction mixture was added with water (100 ml) and diethyl ether (200 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:isopropyl ether=9:1) to obtain the title compound (Intermediate 2, 5.58 g).

Aufarbeitung

  1. extractionextracted with diethyl ether (80 ml×2)
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customA solution obtained
  6. stirring35 ml) under ice cooling and stirring the solution for 15 minutes
  7. stirringThe reaction mixture was stirred for 15 minutes
  8. stirringstirred for 45 minutes
  9. stirringfurther stirred at 60° C. for 15 hours
  10. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  11. customdried
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by flash column chromatography (hexane:isopropyl ether=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-7a64a9ebf8694a818385beed98bcc92b
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470807B2

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