Ethyl bromoacetate → 3-Acetyl-6-methyl-4-oxoheptanoic acid ethyl ester

HRID 220472

Reaktionsgleichung

Reaktionsgleichung von HRID 220472
[CH3:1][CH:2]([CH3:10])[CH2:3][C:4](=[O:9])[CH2:5][C:6](=[O:8])[CH3:7].[H-].[Na+].[CH2:13]([O:15][C:16](=[O:19])[CH2:17]Br)[CH3:14]>O1CCCC1>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][CH:5]([C:6](=[O:8])[CH3:7])[C:4](=[O:9])[CH2:3][CH:2]([CH3:10])[CH3:1])[CH3:14]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 763542,4-Heptanedione, 6-methyl-

Produkt 1

HCID 866416513-Acetyl-6-methyl-4-oxoheptanoic acid ethyl esterAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Add a solution of 6-methylheptane-2,4-dione (5.0 g, 35.16 mmol) in tetrahydrofuran (50 mL) dropwise to a cooled suspension (0° C.) of sodium hydride (1.69 g, 42.2 mmol, 60% dispersion in oil) in tetrahydrofuran (50 mL). After 1 hr., add bromoacetic acid ethyl ester (4.28 mL, 38.68 mmol) dropwise and stir at 0° C. to room temperature over 88 hr. Partition the reaction mixture between ethyl acetate (200 mL) and saturated aqueous ammonium chloride solution (100 mL). Separate the organic layer, dry (sodium sulfate), filter and concentrate. Purify using silica gel chromatography (95:5 hexanes:ethyl acetate) to give 3-acetyl-6-methyl-4-oxoheptanoic acid ethyl ester (5.81 g, 73%). 1H-NMR (400 MHz, CDCl3) δ 4.10 (m, 4H), 2.81 (d, 2H), 2.41 (t, 1H), 2.22 (s, 3H), 1.23 (m, 4H), 0.92 (m, 6H).

Aufarbeitung

  1. customPartition the reaction mixture between ethyl acetate (200 mL) and saturated aqueous ammonium chloride solution (100 mL)
  2. customSeparate the organic layer
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify

Quellen und Nachweise

ORD-Eintrag
ord-a89542bd527947c79ea97fb83ad6b93d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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