Water → 1-(4-Isopropylphenyl)-1-(2-methoxyphenyl)-2-methylpropan-1-ol

HRID 2376295

Reaktionsgleichung

Reaktionsgleichung von HRID 2376295
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1)([CH3:17])[CH3:16].O>C1COCC1>[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])([OH:28])[CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1)([CH3:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 113582-BromoanisoleHCID 42512442-(4-Isobutyrylphenyl)propaneHCID 178418339Butyllithium

Produkt 1

HCID 231138311-(4-Isopropylphenyl)-1-(2-methoxyphenyl)-2-methylpropan-1-olAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-bromoanisole (5.0 g, 26.7 mmol) in THF (50 mL) was added n-butyllithium (1.6 M, 18 mL, 29 mmol) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction solution was added 1-(4-isopropylphenyl)-2-methylpropan-1-one (5.70 g, 30.0 mmol), and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture which was extracted with ethyl acetate, and the combined organic layer was washed with water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 3.4 g (yield 43%) of the title compound. Melting point: 85-86° C. (methanol).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washthe combined organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-fee60b443379464bac99173649cfa70f
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465815B2

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