Acetonitrile → 3-(1-Hydroxymethyl-cyclopropyl)-3-oxo-propionitrile

HRID 453223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453223
[Li+].[CH3:2][CH:3]([N-:5]C(C)C)C.C[O:10][C:11]([C:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1)=O.CC#N>C1COCC1>[OH:17][CH2:16][C:13]1([C:11](=[O:10])[CH2:2][C:3]#[N:5])[CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 2724682Lithium diisopropylamideHCID 22934721Methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Produkt 1

HCID 593940603-(1-Hydroxymethyl-cyclopropyl)-3-oxo-propionitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of LDA (115 mmol) in THF (300 mL), at −78° C., a solution of 1-hydroxymethyl-cyclopropanecarboxylic acid methyl ester (5 g, 28.4 mmol) in CH3CN (5.91 mL, 115 mmol) is added. The reaction is allowed to reach rt. At this point it is quenched with 1N HCl (200 mL) and extracted with EtOAc (200 mL×3). It is then dried and evaporated to give 3-(1-hydroxymethyl-cyclopropyl)-3-oxo-propionitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.26 (s, 2 H) 4.03 (s, 1 H) 3.58 (br. s., 2 H) 1.15-1.16 (m, 2 H) 0.92-0.95 (m, 2 H).

Aufarbeitung

  1. customto reach rt
  2. customAt this point it is quenched with 1N HCl (200 mL)
  3. extractionextracted with EtOAc (200 mL×3)
  4. customIt is then dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d58a5c01b8634f3ba60c2f8bb4f293b3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492393B2

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