Triphenylphosphine → 4-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol ester

HRID 882964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882964
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[N:17]1([CH2:23][CH2:24]O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:24][CH2:23][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:11][CH:10]=2)[O:5]1

Komponenten

6

Edukt 4

HCID 11776Triphenylphosphine2×HCID 611632-Morpholinoethanol2×HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 5363146Diisopropyl azodicarboxylate2×

Produkt 1

HCID 46259104-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol esterAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenol (2.55 g, 11.58 mmol), 2-morpholin-4-ylethanol (1.60 mL, 1.73 g, 13.2 mmol) and triphenyl phosphine (3.64 g, 13.9 mmol) in methylene chloride (60 mL) at 0° C. was added dropwise DIAD (2.82 g, 13.9 mmol). The reaction was allowed to warm to room temperature and stir overnight. After 18 hours, additional portions of triphenyl phosphine (1.51 g, 5.8 mmol), 2-morpholin-4-ylethanol (0.70 mL, 5.8 mmol), and DIAD (1.17 g, 5.8 mmol) were added. After stirring an additional 2 hours at room temperature the reaction was concentrated and the residue purified by flash chromatography (5% to 25% EtOAc in CHCl3) to provide the product as a white solid (2.855 g, 74%).

Aufarbeitung

  1. waitAfter 18 hours
  2. stirringAfter stirring an additional 2 hours at room temperature the reaction
  3. concentrationwas concentrated
  4. customthe residue purified by flash chromatography (5% to 25% EtOAc in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-fd2c8938523b4ddf8ad3908729e70dab
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236799B2

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