Trimethylsilyldiazomethane → Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylate

HRID 1508490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508490
[C:1]([C:4]1[CH:5]=[C:6]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)[O:7][CH:8]=1)([OH:3])=[O:2].[CH3:18][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[CH3:12][C:11]1([CH3:13])[C:14]([CH3:16])([CH3:15])[O:17][B:9]([C:6]2[O:7][CH:8]=[C:4]([C:1]([O:3][CH3:18])=[O:2])[CH:5]=2)[O:10]1

Komponenten

5

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 467390315-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylic acid

Produkt 1

HCID 53217215Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Carboxyfuran-2-boronic acid pinacol ester (200 mg, 0.840 mmol) was dissolved in CH2Cl2 (4 mL) and MeOH (0.444 mL). Trimethylsilyldiazomethane (0.840 mL, 1.680 mmol) was added dropwise. After 45 min, the reaction was quenched with AcOH dropwise until the yellow color disappeared. The reaction was concentrated in vacuo to give methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-furoate. 1H NMR (500 MHz, CDCl3): δ 8.20 (s, 1H); 7.37 (s, 1H); 3.84 (s, 3H); 1.36 (s, 12H).

Aufarbeitung

  1. customthe reaction was quenched with AcOH dropwise until the yellow color
  2. concentrationThe reaction was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d3cca8ccf0940ba8a7653d6d5747f26
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221834B2

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