Water → 4-Isobutyl-dihydro-furan-2-one

HRID 458070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458070
[H-].[Na+].C([O:7][C:8](=[O:18])[CH2:9][CH:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11](O)=O)(C)(C)C.O>C1COCC1>[CH2:14]([CH:10]1[CH2:11][O:18][C:8](=[O:7])[CH2:9]1)[CH:15]([CH3:16])[CH3:17]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24758Sodium hydrideHCID 99427122-Isobutyl-succinic acid-4-t-butyl ester

Produkt 1

HCID 152136444-Isobutyl-dihydro-furan-2-oneAusbeute 104,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Triethyl phosphonoacetate (1.13 mL, 5.70 mmol) was added dropwise to a stirring suspension of sodium hydride (0.22 g of a 60% dispersion in oil, 5.43 mmol) in THF (15 mL) at 0° C. under argon. After 20 minutes, ketone 3 (0.75 g, 5.43 mmol) in THF (6 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 16 hours. Water (5 mL) was added, and the mixture was extracted with ether (15 mL×3). The combined organic fractions were washed with brine and dried (MgSO4). The solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5) to give the ester 4 (0.81 g, 72%) as a colorless oil; Rf(heptane/ethyl acetate, 8:2) 0.66; νmax(film)/cm−1 1715 (C═O), 1652 (C═C); δH (400 MHz; CDCl3): 5.80 (1H, quint, J=2.2, CHCO2Et), 4.15 (2H, q, J=7.1, CO2CH2Me), 2.79 (1H, dd, J=19.5, 8.1), 2.69 (1H, ddt, J=19.8, 7.3, 2.3), 2.47 (1H, dd, J=17.3, 7.2), 2.34 (1H, ddt, J=17.3, 5.6, 1.8), 2.14 (1H, m), 2.02 (1H, m), 1.60–1.22 (8H, m); m/z (ES+) 209 (M+H, 57%), 455 (2M+K, 67).

Aufarbeitung

  1. extractionthe mixture was extracted with ether (15 mL×3)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-90e800f79c6749d780c5b56ab4394afa
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189747B2

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