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Triphenylphosphine → HCID 59678685, Verbindung

HRID 1479253
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1479253
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][CH:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1.[C:14]([N:18]1[C:23](=[O:24])[C:22]([Cl:25])=[C:21](O)[CH:20]=[N:19]1)([CH3:17])([CH3:16])[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[C:14]([N:18]1[C:23](=[O:24])[C:22]([Cl:25])=[C:21]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH:9]([OH:11])[CH3:10])=[CH:12][CH:13]=2)[CH:20]=[N:19]1)([CH3:17])([CH3:15])[CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 17755959HCID 17755959, VerbindungHCID 546869462-tert-Butyl-4-chloro-5-hydroxypyridazin-3(2H)-one

Produkt 1

HCID 59678685HCID 59678685, VerbindungAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To solution of the product of Example 6B (269 mg, 1.48 mmol) and 2-tert-butyl-4-chloro-5-hydroxy-2H-pyridazin-3-one (250 mg, 1.23 mmol) dissolved in anhydrous THF (18.5 mL) was added solid PPh3 (485 mg, 1.85 mmol) and DIAD (0.358 mL, 1.85 mmol). After completion of addition the reaction mixture continued to stir at room temperature. After 20 hours, the reaction mixture was diluted with water. The aqueous layer was separated and extracted with ethyl acetate (3×). All combined organic layers were dried over Na2SO4, filtered, and concentrated to provide an oil. The crude material was purified using silica gel chromatography (1:1 pentane:ethyl acetate) to provide the desired product (234 mg, 0.634 mmol) in 51% yield. 1H (CDCl3 7.71 (1H, s), 7.33 (2H, d, 600 MHz): δ J=8.7 Hz), 6.94 (2H, d, J=8.7 Hz), 5.24 (2H, s), 4.19 (1H, m), 3.95 (1H, dd, J=9.2, 3.1 Hz), 3.81 (1H, dd, J=9.2, 7.7 Hz), 1.62 (9H, s) 1.29 (3H, d, J=6.4 Hz).

Aufarbeitung

  1. additionAfter completion of addition the reaction mixture
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialAll combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide an oil
  8. customThe crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-04fd024eb1fc477787b6502f2633b014
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09408927B2

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