1,10-Phenanthroline → 4-[4-Chloro-1-[(4-methylphenyl)thio]butyl]-1,2-dimethoxybenzene

HRID 1684369

Reaktionsgleichung

Reaktionsgleichung von HRID 1684369
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[O:18][CH3:19].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([Li])CCC.CCCCCC.Br[CH2:46][CH2:47][CH2:48][Cl:49]>O1CCCC1.C(OCC)(=O)C>[Cl:49][CH2:48][CH2:47][CH2:46][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:18][CH3:19])[CH:5]=1)[S:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 13181,10-PhenanthrolineHCID 80061-Bromo-3-chloropropaneHCID 105164711,2-Dimethoxy-4-[[(4-methylphenyl)thio]methyl]benzeneHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 108317364-[4-Chloro-1-[(4-methylphenyl)thio]butyl]-1,2-dimethoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 13.72 g of 1,2-dimethoxy-4-[[(4-methylphenyl)thio]methyl]benzene and a crystal of phenanthroline in 250 mL of tetrahydrofuran (dried over 3A sieves), under nitrogen at -78° C., is added 21.0 mL of 2.5M n-butyl lithium/hexane via a syringe. After 10 minutes, the brown solution is warmed to 0° C. for 1 hour, then it is recooled to -78° C. and 8.02 mL of 1-bromo-3-chloropropane is added via syringe. The reaction is permitted to warm to room temperature overnight. To the now light yellow reaction mixture is added 10 mL of ethyl acetate and the resulting solution concentrated in vacuo. The residue is partitioned between ethyl acetate and water, the organic phase dried (sodium sulfate) and concentrated in yacuo to a yellow oil. Purification by chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol, repeated three times, affords 16.47 g of the desired product as a yellow oil.

Aufarbeitung

  1. customis recooled to -78° C.
  2. temperatureto warm to room temperature overnight
  3. concentrationthe resulting solution concentrated in vacuo
  4. customThe residue is partitioned between ethyl acetate and water
  5. dry with materialthe organic phase dried (sodium sulfate)
  6. concentrationconcentrated in yacuo to a yellow oil
  7. customPurification by chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-8fbdda7b0f364c09b351f7e30cd22ed5
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639887

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