Triphenylphosphine → HCID 86711734, Verbindung

HRID 528447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528447
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[N:3]=1.C([CH:13](O)[C:14]([O-:16])=[O:15])C.[C:18]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:19]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH2:18]([O:16][C:14](=[O:15])[CH2:13][O:9][C:5]1[C:4]([Cl:10])=[N:3][C:2]([Cl:1])=[N:7][C:6]=1[Cl:8])[CH3:19]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 4071895Alpha-HydroxybutyrateHCID 5363146Diisopropyl azodicarboxylateHCID 866673322,4,6-Trichloropyrimidin-5-ol

Produkt 1

HCID 86711734HCID 86711734, VerbindungAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2,4,6-trichloro-pyrimidin-5-ol (3.0 g, 15.0 mmol), ethylglycolate (16.7 mL, 17.3 mmol), triphenylphosphine (4.5 g, 17.3 mmol) and DIAD (3.4 mL, 17.3 mmol) in dioxane (100 mL) was stirred at RT for 18 hours then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0-15% ethyl acetate in cyclohexane) affording (2,4,6-Trichloro-pyrimidin-5-yloxy)-acetic acid ethyl ester as a white solid (2.67 g, 62%). 1H NMR (400 MHz, CDCl3): δ 4.77 (2H, s), 4.28 (2H, q, J=7.14 Hz), 1.32 (3H, t, J=7.15 Hz).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, gradient 0-15% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-e3ad15d2d9874199aa1fbd02a0cb7e90
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346817B2

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