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Hydrochloric Acid → 7,8-Difluoro-2-pentyl-5-(4-propylcyclohexylethynyl)chroman-6-ol

HRID 2244842
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2244842
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4](I)[C:3]=1[OH:19].[C:20]([CH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]1)#[CH:21].Cl>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]([C:21]#[C:20][CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]2)[C:3]=1[OH:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 218706261-Ethynyl-4-propylcyclohexaneHCID 592152577,8-Difluoro-5-iodo-2-pentylchroman-6-ol

Produkt 1

HCID 592152687,8-Difluoro-2-pentyl-5-(4-propylcyclohexylethynyl)chroman-6-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

8.0 g (20.9 mmol) of 7,8-difluoro-5-iodo-2-pentylchroman-6-ol are stirred at 50° C. for 19 h together with 4.72 g (31.4 mmol) of 1-ethynyl-4-propylcyclohexane in the presence of 441 mg (0.63 mmol) of bis(triphenylphosphine)palladium(II) chloride and 120 mg (0.63 mmol) of copper(I) iodide in 90 ml of triethylamine. After cooling, the batch is added to ice/water and acidified using hydrochloric acid. The mixture is extracted a number of times with MTBE, and the combined extracts are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, 1-chlorobutane). The phenol obtained is used directly for the following reaction.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted a number of times with MTBE
  3. washthe combined extracts are washed with water and sat. sodium chloride soln
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by column chromatography (SiO2, 1-chlorobutane)

Quellen und Nachweise

ORD-Eintrag
ord-3d18bb44540243279dc087295fe9109e
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07678929B2

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