Sodium hydride → 2-Chloro-5-cyclopentyl-5-hydroxy-3-oxo-non-8-ynoic Acid Methyl Ester

HRID 858869

Reaktionsgleichung

Reaktionsgleichung von HRID 858869
[H-].[Na+].[CH3:3][O:4][C:5](=[O:11])[CH:6]([Cl:10])[C:7]([CH3:9])=[O:8].C([Li])CCC.[CH:17]1([C:22](=[O:27])[CH2:23][CH2:24][C:25]#[CH:26])[CH2:21][CH2:20][CH2:19][CH2:18]1>C1COCC1>[CH3:3][O:4][C:5](=[O:11])[CH:6]([Cl:10])[C:7](=[O:8])[CH2:9][C:22]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)([OH:27])[CH2:23][CH2:24][C:25]#[CH:26]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 107332Methyl 2-chloroacetoacetateHCID 224997991-Cyclopentyl-pent-4-yn-1-oneHCID 178418339Butyllithium

Produkt 1

HCID 587622142-Chloro-5-cyclopentyl-5-hydroxy-3-oxo-non-8-ynoic Acid Methyl EsterAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A slurry of NaH (3.2 g, 60% suspension in mineral oil, 80 mmol) in dry THF (250 mL) was cooled to −40° C. Methyl-2-chloroacetoacetate (9.74 mL, 80 mmol) was added slowly. The reaction was stirred until all gas evolution had ceased, and then butyl lithium (2.5 M, 32 mL, 80 mmol) was added. The reaction was stirred for 10 minutes, and then 1-cyclopentyl-pent-4-yn-1-one (4.0 g, 27 mmol) from Step 2 above, was added as a solution in 20 mL THF. The reaction was stirred 1 hour, and then warmed to room temperature. The reaction was quenched with 1 N HCl (200 mL) and the layers were separated. The aqueous layer was extracted with CH2Cl2 and the organic layers were combined. The organic layer was washed with water, and then concentrated by rotary evaporation. The crude product was purified by chromatography to yield the pure product (6.345 g, 78% yield).

Aufarbeitung

  1. stirringThe reaction was stirred for 10 minutes
  2. stirringThe reaction was stirred 1 hour
  3. customThe reaction was quenched with 1 N HCl (200 mL)
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. washThe organic layer was washed with water
  7. concentrationconcentrated by rotary evaporation
  8. customThe crude product was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b59773e611954f21b3c2956d019dd6e7
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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