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Hydrochloric Acid → HCID 178441218, Verbindung

HRID 2168573
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2168573
C(C1C=CC(CN)=CC=1)=C.[C:11]1([P:17]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C-:18]2[CH:22]=[C:21]([C:23]([CH3:33])([CH2:25]C[CH:27]3OCCC[O:28]3)[CH3:24])[CH:20]=[C:19]2[P:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:53]([C:57]1[CH:58]=[C:59]([P:75]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C-:60]([P:62]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:61]=1)([CH3:56])([CH3:55])[CH3:54].[Fe+2:88].Cl>C1COCC1>[C:63]1([P:62]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C-:60]2[CH:61]=[C:57]([C:53]([CH3:56])([CH2:54][CH:27]=[O:28])[CH3:55])[CH:58]=[C:59]2[P:75]([C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)[C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.[C:23]([C:21]1[CH:20]=[C:19]([P:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C-:18]([P:17]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:22]=1)([CH3:33])([CH3:24])[CH3:25].[Fe+2:88]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 110734664-Vinylbenzylamine (stabilized with MEHQ)HCID 178441217HCID 178441217, Verbindung

Produkt 1

HCID 178441218HCID 178441218, VerbindungAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

For the deprotection leading to the actual compound of formula (9), with E=(CH2)3 and GF=4-vinyl-benzylamine, a solution of 1,1′,2,2′-tetrakis(diphenyl-phosphino)-4-[4-(1,3-dioxan-2-yl)-2-methylbut-2-yl]-4′-tert-butylferrocene (0.1 g, 88 μmol) in 20 ml of THF is admixed with 5 ml of 2N hydrochloric acid solution. The solution is placed under microwave radiation (125 W) according to the following program: temperature rise 10° C./min to 120° C., then plateau at 120° C. for 10 min. After cooling, the reaction mixture is concentrated under vacuum, diluted with 20 ml of water, and extracted with 2 times 25 ml of CH2Cl2. The organic phase is dried over MgSO4 and concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel (eluent AcOEt/heptane 1:4) to give 90 mg (ρ=90%) of 1,1′,2,2′-tetrakis(diphenylphosphino)-4-(4-oxo-2-methylbut-2-yl)-4′-tert-butylferrocene in the form of a red powder, for which the 31P NMR spectrum preserves, as expected, the ABCD spin system appearance, with slightly modified chemical shifts.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated under vacuum
  3. additiondiluted with 20 ml of water
  4. extractionextracted with 2 times 25 ml of CH2Cl2
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customis purified by chromatography on silica gel (eluent AcOEt/heptane 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-47dd5bbfecb946b5826194942e8002d6
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09045511B2

Notizen zur Reaktion

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