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Water → HCID 70938331, Verbindung

HRID 469160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 469160
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.[CH3:25][C:26]1([CH3:40])[C:30]([CH3:32])([CH3:31])[O:29][B:28]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[O:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(Cl)Cl>[CH3:16][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:13])=[O:14])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:37][C:36]2[CH:38]=[CH:39][C:33]([B:28]3[O:27][C:26]([CH3:40])([CH3:25])[C:30]([CH3:31])([CH3:32])[O:29]3)=[CH:34][CH:35]=2)[CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 5049666Sodium triacetoxyborohydrideHCID 593426022',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)biphenyl-3-carbaldehyde

Produkt 1

HCID 70938331HCID 70938331, VerbindungAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2′,6′-dimethyl-4′-(3-(methylsulfonyl)propoxy)-[1,1′-biphenyl]-3-carbaldehyde (1.0 g) synthesized according to a method described in [WO 2008/001931 pamphlet, (Reference Example 18)] and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.63 g) were dissolved in methylene chloride (10 mL), and to the resultant solution, sodium triacetoxyborohydride (1.84 g) was added, followed by stirring the resultant reaction mixture at room temperature for 14 hours. To the reaction mixture, water (20 mL) was added, followed by extracting the reaction mixture with methylene chloride (20 mL) twice, and the resultant organic phase was washed sequentially with water (50 mL) and a saturated saline (50 mL) and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure to obtain the subject compound (1.4 g) as a colorless amorphous solid.

Aufarbeitung

  1. customreaction mixture at room temperature for 14 hours
  2. extractionby extracting the reaction mixture with methylene chloride (20 mL) twice
  3. washthe resultant organic phase was washed sequentially with water (50 mL)
  4. dry with materiala saturated saline (50 mL) and was dried over anhydrous sodium sulfate
  5. distillationFrom the organic phase, the solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2ca9857ca2db4a1d9ae9061987fac7fc
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629102B2

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