Methyl iodide → 4-(1,1-Dimethyl-2-butynyl)anisole

HRID 481524

Reaktionsgleichung

Reaktionsgleichung von HRID 481524
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])[CH:3]=[C:4](Br)Br.[Li][CH2:17]CCC.CI>C1COCC1>[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])[C:3]#[C:4][CH3:17]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 190664224-(1,1-Dimethyl-3,3-dibromo-2-propenyl)anisoleHCID 178418339Butyllithium

Produkt 1

HCID 190665084-(1,1-Dimethyl-2-butynyl)anisoleAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of Compound 53 (335 mg, 1.00 mmol) in THF (10 ml) was added n-BuLi (1.69M in hexane, 1.19 ml, 2.01 mmol) at -78° C. under N2, then warmed up to 0° C., and stirred for 1.5 h. MeI (213 mg, 1.50 mmol) was added, and stirred for 1.5 h at 0° C. The mixture was quenched by the addition of NH4Cl aq., and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 54 (162 mg, 86%) as a colorless oil.

Aufarbeitung

  1. stirringstirred for 1.5 h at 0° C
  2. customThe mixture was quenched by the addition of NH4Cl aq.
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis was purified by SiO2 chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2ea3746090b5481bb563e3337c69d2d3
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789423

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