Chlorodicyclohexylphosphine → 2-(Dicyclohexylphosphino)-2'-methoxybiphenyl

HRID 1296994

Reaktionsgleichung

Reaktionsgleichung von HRID 1296994
CC1C=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17](C)=[CH:16][CH:15]=2)[C:9](=[O:13])[CH:10]([CH3:12])C)=CC=1.[Li][CH2:22]CCC.Cl[P:27]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[CH:28]1([P:27]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:8]2[CH:5]=[CH:6][CH:12]=[CH:10][C:9]=2[O:13][CH3:22])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

5

Edukt 3

HCID 2734135ChlorodicyclohexylphosphineHCID 120407443-Methyl-1,1-bis(4-methylphenyl)-2-butanoneHCID 178418339Butyllithium

Produkt 1

HCID 117941862-(Dicyclohexylphosphino)-2'-methoxybiphenylAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1 (535 mg, 2.03 mmol) in THF (20 mL) was cooled to −78° C. under argon, then n-BuLi (1.6 M in hexane, 1.35 mL, 2.16 mmol) was added dropwise. After 2.5 h at −78° C., a solution of chlorodicyclohexylphosphine (570 mg, 2.45 mmol) in THF (3 mL) was added over 10 min. The reaction mixture was then allowed to warm to room temperature overnight, then quenched with saturated aqueous NaHCO3 and concentrated in vacuo. The resulting aqueous suspension was extracted with ether (2×50 mL), and the combined ethereal layers were dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude solid was recrystallized from ethanol to afford 420 mg (54%) of a white solid.

Aufarbeitung

  1. customquenched with saturated aqueous NaHCO3
  2. concentrationconcentrated in vacuo
  3. extractionThe resulting aqueous suspension was extracted with ether (2×50 mL)
  4. dry with materialthe combined ethereal layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-fe8460489d354aa6ae274ba3b356465a
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07247731B2

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