Thiophenol → (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

HRID 2368868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368868
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:21]([CH3:22])=[CH:20][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)=[CH:7][C:6]=1[CH3:23].C1CCC(N=C=NC2CCCCC2)CC1.[C:39]1([SH:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:23])=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14](=[O:16])[S:45][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:20][C:21]=1[CH3:22]

Komponenten

6

Edukt 3

HCID 7969ThiophenolHCID 10868DicyclohexylcarbodiimideHCID 67262065(E)-3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

Produkt 1

HCID 86672878(E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (E)-3-[4-(methoxymethoxy)-3,5-dimethylstyryl]benzoic acid (0.1 g, 0.320 mmol) in DCM (5 mL) were added DCC (72.6 mg, 0.352 mmol), DMAP (7.9 mg, 0.064 mmol), and benzenethiol (65.7 μL, 0.640 mmol) at room temperature. The reaction mixture was stirred overnight (about 18 hours) and filtered through Celite. The filtrate was washed with 10% citric acid, brine, and dried with Na2SO4. The solution was filtered and concentrated. The compound was purified by column chromatography (9:1 Hexane:EtOAc) to afford (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate in quantitative yield.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with 10% citric acid, brine
  3. dry with materialdried with Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customThe compound was purified by column chromatography (9:1 Hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-208e80c956a5438cb63a2877faf503d5
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703815B2

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