Ammonium Chloride → HCID 58036795, Verbindung

HRID 1028361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028361
[Li][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:8]1([P:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH4+].[Cl-]>C1COCC1>[C:25]1([P:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[NH:23][CH:22]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:21]=[CH:20]3)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 6286598-(Diphenylphosphino)quinolineHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 58036795HCID 58036795, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

PhLi (0.56 mL, 1.8M in di-n-butyl ether, 1 mmol) was added to a stirred solution of 8-diphenylphoshinoquinoline (1) (156 mg, 0.5 mmol) in dry THF (5 mL) at −78° C. and the solution was stirred at 0° C. for 10 minutes. The solution was then cooled to −78° C., saturated aqueous NH4Cl solution (10 mL) was added and the mixture was warmed to room temperature. Products were extracted with EtOAc, washed with water and saturated aqueous NaCl, dried (MgSO4) and evaporated to give 4 (196 mg) quantitatively as a yellow oil. 1H NMR (400.13 MHz, CDCl3) δ 7.4-7.3 (m, 15H, Ph-H), 6.92 (d, 1H, J=7.2 Hz, C5—H), 6.69 (ddd, 1H, J=7.2, 6.0, 1.2 Hz, C7—H), 6.54 (t, 1H, J=7.2 Hz, C6—H), 6.38 (d, 1H, J=9.6 Hz, C4—H), 5.64 (dd, 1H, J=10.0, 4.0 Hz, C3—H), 5.44 (bs, 1H, N1—H), 5.15 (d, 1H, J=7.2 Hz, C2—H) ppm; 13C NMR (100.61 MHz, CDCl3) δ 146.5 (d, J=19.2 Hz), 145.1, 135.4 (d, J=8.1 Hz), 135.3 (d, J=7.1 Hz), 134.5, 133.7 (d, J=18.2 Hz), 133.6 (d, J=19.2 Hz), 133.4 (d, J=19.2 Hz), 127.3, 128.7-128.3 (m), 127.1, 126.0, 125.2, 124.5, 119.1, 117.1, 116.1 (d, J=8.1 Hz), 57.6 ppm; 31P NMR (161.97 MHz, CDCl3) δ −23.8 ppm.

Aufarbeitung

  1. temperatureThe solution was then cooled to −78° C.
  2. temperaturethe mixture was warmed to room temperature
  3. extractionProducts were extracted with EtOAc
  4. washwashed with water and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f61f2c624b0c4c3cbf700f4ea0bea296
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735583B2

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