Toluene → 4-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one

HRID 634370

Reaktionsgleichung

Reaktionsgleichung von HRID 634370
[Br-].[CH3:2][N:3]([CH3:25])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[OH:43][CH:44]([C:46]1[O:47][C:48](=[O:63])[C:49]2[C:54]([C:55]=1[C:56]1[S:60][C:59]([CH:61]=O)=[CH:58][CH:57]=1)=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH3:45].[NH4+].[Cl-]>O1CCOCC1.CCOC(C)=O>[CH3:2][N:3]([CH3:25])[CH2:4][CH:5]=[CH:61][C:59]1[S:60][C:56]([C:55]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48](=[O:63])[O:47][C:46]=2[CH:44]([OH:43])[CH3:45])=[CH:57][CH:58]=1

Komponenten

8

Edukt 5

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 118131138HCID 118131138, Verbindung

Produkt 1

HCID 1237356434-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-oneAusbeute 40.858,102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

In a 100 ml 3-necked round bottomed flask (2-(dimethylamino)ethyl)-triphenylphosphonium bromide (1569 mg, 3.79 mmol) was loaded and suspended under Argon in 15 ml of Dioxane. Potassium bis(trimethylsilyl)amide solution 0.5 M in toluene (6.0 ml, 3.03 mmol) was added drop wise and a yellow\orange color appeared. The mixture was further stirred for 20 min then 5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde (Intermediate B37, 455 mg, 1.515 mmol) dissolved in 5 ml of dioxane was added The mixture was further stirred at rt for 2 h then poured into 100 ml of NH4Cl sat. sol. and 200 ml of EtOAc. Phases were separated and the organic one was dried over sodium sulfate. Solvents were removed and the crude was purified by chromatography eluting with DCM\20% MeOH in DCM mixtures to leave 4-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (220 mg, 0,619 mmol, 40.9% yield) as a yellow oil.

Aufarbeitung

  1. additionwas added The mixture
  2. stirringwas further stirred at rt for 2 h
  3. customPhases were separated
  4. dry with materialthe organic one was dried over sodium sulfate
  5. customSolvents were removed
  6. customthe crude was purified by chromatography
  7. washeluting with DCM\20% MeOH in DCM mixtures

Quellen und Nachweise

ORD-Eintrag
ord-c0c148c6293e483e94d77d900dc22546
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321776B2

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