Tetrahydrofuran → HCID 178472396, Verbindung

HRID 2095644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095644
I[C:2]1[CH:3]=[N:4][N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:6]=1[CH3:7].C1COCC1.C([Mg]Cl)(C)C.CO[B:31]1[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]1>>[CH3:7][C:6]1[N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)[N:4]=[CH:3][C:2]=1[B:31]1[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]1

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, VerbindungHCID 178472422HCID 178472422, Verbindung

Produkt 1

HCID 178472396HCID 178472396, Verbindung

Versuchsvorschrift

To a solution of ethyl trans-4-(4-iodo-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylate (100.0 mg, 0.2761 mmol) in THF (5 mL, 60 mmol) was added 2 M isopropylmagnesium chloride in THF (0.5522 mL, 1.104 mmol) at rt, and the mixture was stirred for 30 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.2262 mL, 1.380 mmol) was added, and the mixture stirred at rt for 2 h. The reaction was quenched with sat. NH4Cl, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was concentrated in vacuo to afford the title compound as a clear oil. The material was used in the next step without further purification.

Aufarbeitung

  1. stirringthe mixture stirred at rt for 2 h
  2. customThe reaction was quenched with sat. NH4Cl
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. concentrationthe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-51ab2498bf554f2e963cc3d64b971cdc
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445510B2

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