Tris(hydroxymethyl)aminomethane → Tert-butyl 2-methylbutanoate

HRID 2193011

Reaktionsgleichung

Reaktionsgleichung von HRID 2193011
[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[CH3:8][C:9]([CH3:12])([O-])[CH3:10].[K+].C(O)C(N)(CO)CO>C(Cl)Cl>[CH3:1][CH:2]([CH2:6][CH3:7])[C:3]([O:5][C:9]([CH3:12])([CH3:10])[CH3:8])=[O:4]

Komponenten

5

Edukt 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 83142-Methylbutanoic AcidHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 523483Tert-butyl 2-methylbutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2-methylbutanoic acid (1.029 Ml, 8.29 mmol) in DCM (10 Ml) was added potassium tert-butoxide (20 wt % in THF) (4.66 Ml, 8.29 mmol) dropwise at 0° C. The resulting suspension was allowed to warm to room temperature, and stirred for 1.5 hr. The reaction mixture was diluted with DCM (10 Ml), MP-®Trisamine Resin (3.86 g, 3.22 mMol/g; Argonaut Technologies, Inc.) was added, and the resulting suspension was stirred at room temperature for 1.5 hours. The resin was removed by vacuum filtration, and the resulting filtrate was washed with 1 N NaOH (1×20 Ml). The organic layer was dried over magnesium sulfate, filtered, and concentrated to afford tert-butyl 2-methylbutanoate. 1H NMR (500 MHz, CDCl3) δ 2.24 (sextet, 1H), 1.61 (m, 1H), 1.44-1.39 (overlapping s, m, 10H), 1.09 (d, 3H), 0.90 (t, 3H).

Aufarbeitung

  1. additionwas added
  2. stirringthe resulting suspension was stirred at room temperature for 1.5 hours
  3. customThe resin was removed by vacuum filtration
  4. washthe resulting filtrate was washed with 1 N NaOH (1×20 Ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dca8fe0f0dc64c51a32c3697e7d08d51
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329722B2

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