Reacción #611739

ord-fea611f7a1da4a03bd46a8456df9a528

Ecuación de reacción

C#CCCCC(=O)O
hex-5-ynoic acid
CCN=C=NCCCN(C)C.Cl
EDC.HCl
COCCNCCOC
bis(2-methoxyethyl)amine
C#CCCCC(=O)N(CCOC)CCOC
title compound
C#CCCCC(=O)N(CCOC)CCOC
N,N-bis(2-Methoxyethyl)hex-5-ynamide

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowas then washed with hydrochloric acid (1 M, 2×500 mL) and water (500 mL)
  2. 2
    OtroThe organic layer was dried
  3. 3
    Otroevaporated in vacuo

Procedimiento

To a solution of hex-5-ynoic acid (7.11 g, 63.4 mmol), EDC.HCl (14.0 g, 72.9 mmol) and DMAP (387 mg, 3.17 mmol) in DCM (600 mL) at 0° C. was added bis(2-methoxyethyl)amine (9.3 mL, 63 mmol). The resulting mixture was warmed to RT for 20 hr and was then washed with hydrochloric acid (1 M, 2×500 mL) and water (500 mL). The organic layer was dried and evaporated in vacuo to afford the title compound, Intermediate B, as a yellow oil (16 g, 97%): 1H NMR (400 MHz, CDCl3) δ: 1.88 (3H, m), 2.26 (2H, m), 2.49 (2H, m), 3.32 (6H, s), 3.51 (4H, m), 3.55 (4H, m)

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09340545B2uspto-grants-2016_05