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Tetrahydrofuran → HCID 178421687, Verbindung

HRID 2095677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2095677
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH3:20])=[C:18](I)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1.C([Mg]Cl)(C)C.CO[B:34]1[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]1.[NH4+].[Cl-]>>[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH3:20])=[C:18]([B:34]3[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]3)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, VerbindungHCID 178429782HCID 178429782, Verbindung

Produkt 1

HCID 178421687
HCID 178421687, Verbindung

Versuchsvorschrift

To a solution of 1-(cis-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-5-methyl-1H-pyrazole (870.0 mg, 2.069 mmol) in THF (20 mL, 200 mmol) at rt was added 1.3 M of isopropylmagnesium chloride in THF (6.367 mL, 8.278 mmol), and the mixture was stirred for 1 h. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.696 mL, 10.35 mmol), and allowed to stir at rt for 1 h. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. The organic layer was concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=0.12 (s, 6H), 0.97 (s, 9H), 1.33 (s, 9H), 1.60-1.75 (m, 4H), 1.83-1.92 (m, 2H), 2.32-2.40 (m, 2H), 2.47 (s, 3H), 4.07-4.21 (m, 2H), 7.58 (s, 1H).

Aufarbeitung

  1. stirringto stir at rt for 1 h
  2. customthe organic solvent was removed in vacuo
  3. extractionThe material was extracted with DCM and water
  4. concentrationThe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eb85f11cbdf34a9db6489e575028b162
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08445510B2

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