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(2-(Benzyloxy)biphenyl-3-yl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol → 3'-((2-(Benzyloxy)biphenyl-3-yl)(phenyl)methyl)-2-methoxybiphenyl

HRID 45462
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 45462
[CH2:1]([O:8][C:9]1[C:14]([C:15]([C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[CH:26]=[CH:27][CH:28]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)=[CH:13][CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.[PH2](O)=O>[CH2:1]([O:8][C:9]1[C:14]([CH:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[CH:26]=[CH:27][CH:28]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 58238602(2-(Benzyloxy)biphenyl-3-yl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol

Produkt 1

HCID 582385813'-((2-(Benzyloxy)biphenyl-3-yl)(phenyl)methyl)-2-methoxybiphenylAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 4124402Phosphinic AcidLösungsmittel

Versuchsvorschrift

A solution of 26 (0.85 g, 1.55 mmol) in acetonitrile (50 mL) and 50% aqueous hypophosphorous acid (21 mL) was kept at reflux for 3.5 hr. The acetonitrile was removed in vacuo, the residue was diluted with ethyl acetate (150 mL) and water (80 mL). Phases were separated. The organic phase was washed with saturated sodium bicarbonate (2×80 mL) and water (2×80 mL) dried over sodium sulfate and filtered. The solvent was removed on a rotary evaporator. The crude product was purified by chromatography on silica (45 g) with 2% ethyl acetate in heptane (4 L) to yield pure D2 (0.42 g, 69%).

Aufarbeitung

  1. temperatureat reflux for 3.5 hr
  2. customThe acetonitrile was removed in vacuo
  3. additionthe residue was diluted with ethyl acetate (150 mL) and water (80 mL)
  4. customPhases were separated
  5. washThe organic phase was washed with saturated sodium bicarbonate (2×80 mL) and water (2×80 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed on a rotary evaporator
  9. customThe crude product was purified by chromatography on silica (45 g) with 2% ethyl acetate in heptane (4 L)

Quellen und Nachweise

ORD-Eintrag
ord-6b5b296a370f4011ad147b42294e8195
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541522B2

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