Tetrahydrofuran → HCID 178459279, Verbindung

HRID 1483825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483825
[OH:1][C@H:2]1[CH2:7]C[C@H](C(OCC)=O)C[CH2:3]1.C[Mg]Br.[CH3:16][C:17](=O)OCC.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[OH:1][C:2]([C@H:26]1[CH2:17][CH2:16][C@H:24]([OH:25])[CH2:23][CH2:22]1)([CH3:7])[CH3:3]

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 178418573HCID 178418573, VerbindungHCID 178472487HCID 178472487, Verbindung

Produkt 1

HCID 178459279HCID 178459279, VerbindungAusbeute 96 %

Versuchsvorschrift

To a solution of trans-ethyl 4-hydroxycyclohexanecarboxylate (1 g, 5.8 mmol) in THF (50 mL) was added dropwise methylmagnesium bromide (7.7 mL, 23.2 mmol) at −78° C. The mixture was stirred at room temperature for 2 h. TLC (PE:EA=1:1) showed the reaction was complete. The mixture was quenched by the addition of NH4Cl (100 mL) and extracted with EtOAc (100 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give trans-4-(2-hydroxypropan-2-yl)cyclohexanol (0.88 g, 96%) as a yellow solid.

Aufarbeitung

  1. customThe mixture was quenched by the addition of NH4Cl (100 mL)
  2. extractionextracted with EtOAc (100 mL*3)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0fb524c1e6249658041835e904a1e51
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416132B2

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