Dichloromethane → 4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carbaldehyde

HRID 1662531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662531
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH2:23][OH:24])[CH:9]=1)([CH3:4])[CH3:3].C(Cl)Cl.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC1(C)N([O])C(C)(C)CCC1>CCOC(C)=O>[CH3:4][C:2]([Si:5]([CH3:25])([CH3:26])[O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:23]=[O:24])[C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:12][CH:13]=1)([CH3:1])[CH3:3]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 2724126TempoHCID 12217721Iodo benzene diacetateHCID 57706179(4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)methanol

Produkt 1

HCID 577066184-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carbaldehydeAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 200 mL round bottom flask was charged with 83.18B (1.21 g, 3.21 mmol), DCM (9 mL), iodobenzene diacetate (available from Aldrich) (1.24 g, 3.86 mmol), and TEMPO (available from Aldrich) (0.0502 g, 0.321 mmol). The solution was stirred for 2 hours at room temperature and diluted with EtOAc. The organic phase was washed with saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 83.18C (1.05 g, 87% yield) as a colorless oil.

Aufarbeitung

  1. washThe organic phase was washed with saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-86b05b8e30164787a3d4d23d90f58f92
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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