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Hydrochloric Acid → (2',4',6'-Triisopropylbiphenyl-2-yl)phosphine

HRID 1049629
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1049629
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[PH:22](=O)OCC)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl[Si](C)(C)C.[PH2](=O)[O-].Cl>CCOC(C)=O.C1COCC1>[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:7]=[C:6]([CH:13]([CH3:14])[CH3:15])[C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[PH2:22])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 4413076CID 4413076HCID 86661506Lithium aluminum hydride chlorotrimethylsilaneHCID 178476781HCID 178476781, Verbindung

Produkt 1

HCID 58067324(2',4',6'-Triisopropylbiphenyl-2-yl)phosphineAusbeute 156,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of ethyl 2′,4′,6′-triisopropylbiphenyl-2-ylphosphinate (17.5 g, 47.0 mmol, 1.0 equiv) in 100 mL of anhydrous, degassed THF was cooled to 0° C. under an atmosphere of nitrogen. The lithium aluminum hydride/chlorotrimethylsilane solution was transferred by cannula into the solution of phosphinate over 20 min. The reaction was allowed to proceed overnight with slow warming to 22° C. Prior to quench the mixture was cooled in an ice bath. The reaction was quenched by slow addition of EtOAc (23 mL, 235 mmol, 5 equiv), followed by aqueous hydrochloric acid (2 M, 250 mL, 500 mmol, 10.6 equiv). This mixture was allowed to stir for 1 h under an atmosphere of N2. This mixture was diluted with EtOAc (250 mL), the layers were separated and the organic layer was washed once with a saturated solution of NaCl (100 mL). The organic solution was concentrated in vacuo to give a white solid (23.0 g) which was 66% potent (w/w by HPLC), for a 99% yield. This material was used without further purification.

Aufarbeitung

  1. temperaturewith slow warming to 22° C
  2. customPrior to quench the mixture
  3. temperaturewas cooled in an ice bath
  4. customthe layers were separated
  5. washthe organic layer was washed once with a saturated solution of NaCl (100 mL)
  6. concentrationThe organic solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f70791f56bf64f4cb052691f1999c68f
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09381508B2

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