4-Methoxybenzyl alcohol → HCID 70497530, Verbindung

HRID 333647

Reaktionsgleichung

Reaktionsgleichung von HRID 333647
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[Cl:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:53][O:54][C:55]1[CH:62]=[CH:61][C:58]([CH2:59]O)=[CH:57][CH:56]=1>C1COCC1>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([O:20][CH2:59][C:58]2[CH:61]=[CH:62][C:55]([O:54][CH3:53])=[CH:56][CH:57]=2)=[O:19])[C:3]=1[Cl:21]

Komponenten

6

Edukt 4

HCID 77384-Methoxybenzyl alcoholHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 25181547Halauxifen

Produkt 1

HCID 70497530HCID 70497530, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinic acid (600 mg, 1.81 mmol) in THF (10 mL) was added triphenylphosphine (475 mg, 1.81 mmol), diethyl azodicarboxylate (0.29 mL, 1.81 mmol), and 4-methoxybenzyl alcohol (0.34 mL, 2.72 mmol). The reaction mixture was stirred for 48 h. Additional triphenylphosphine (475 mg, 1.81 mmol) was added to the reaction, and the reaction mixture was stirred for 24 h. The reaction mixture was concentrated to dryness and was purified by silica gel chromatography (eluting with a 0-100% EtOAc/hexane gradient) to provide an off-white solid (170 mg, 26%): mp 73-83° C.; 1H NMR (400 MHz, CDCl3) δ 7.66 (dd, J=8.6, 7.8 Hz, 1H), 7.45-7.38 (m, 2H), 7.22 (dd, J=8.7, 1.8 Hz, 1H), 7.16 (d, J=1.7 Hz, 1H), 6.94-6.87 (m, 2H), 5.38 (s, 2H), 4.80 (s, 2H), 3.96 (d, J=0.8 Hz, 3H), 3.81 (s, 3H); ESIMS m/z 451 ([M+H]+), 449 ([M−H]−).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 24 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customwas purified by silica gel chromatography (
  4. washeluting with a 0-100% EtOAc/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-567ecb0ca2894d9e944c5c3a8e11737f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883688B2

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