4-tert-Butylcyclohexanone → Cyclohexane, 1-(1,1-dimethylethyl)-4-methylene-

HRID 525482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525482
[Li][CH2:2]CCC.[C:6]([CH:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([CH:10]1[CH2:15][CH2:14][C:13](=[CH2:2])[CH2:12][CH2:11]1)([CH3:9])([CH3:8])[CH3:7]

Komponenten

5

Edukt 2

HCID 73924-tert-ButylcyclohexanoneHCID 178418339Butyllithium

Produkt 1

HCID 139425Cyclohexane, 1-(1,1-dimethylethyl)-4-methylene-Ausbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of methyltriphenylphosphonium bromide (5.36 g, 15 mmol, 1.5 eq) in dried THF (40 mL) was added n-BuLi (2.5 M) (6 mL, 15 mmol, 1.5 eq) at −78° C. The mixture was stirred at room temperature for 1 h. The solution of 4-(tert-butyl)cyclohexanone (1.54 g, 10 mmol) in THF (10 mL) was added to the reaction mixture at −78° C. The mixture was stirred at 70° C. for 12 h. The solvent was removed and the residue was suspended in hexane. The mixture was filtered, and the filtrate was concentrated to give 1-(tert-butyl)-4-methylenecyclohexane as yellow oil (0.80 g, yield: 50%). 1HNMR (400 MHz, CDCl3) δ: 4.58 (s, 2H), 2.34-2.31 (m, 2H), 2.01-1.95 (m, 2H), 1.88-1.84 (m, 2H), 1.14-1.06 (m, 3H), 0.86 (s, 9H).

Aufarbeitung

  1. stirringThe mixture was stirred at 70° C. for 12 h
  2. customThe solvent was removed
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c2b5f165b9cf44fab989c480574bd61c
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340527B2

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