2-Thiopheneethanol → 1-Benzhydryl-3-(2-(thiophen-2-yl)ethoxy)azetidine

HRID 2172037

Reaktionsgleichung

Reaktionsgleichung von HRID 2172037
CS([O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:28][CH2:29]O>>[CH:10]([N:8]1[CH2:9][CH:6]([O:5][CH2:29][CH2:28][C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[CH2:7]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

3

Edukt 2

HCID 794002-ThiopheneethanolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Produkt 1

HCID 671545391-Benzhydryl-3-(2-(thiophen-2-yl)ethoxy)azetidine

Versuchsvorschrift

A solution of 1-benzhydrylazetidin-3-yl methanesulfonate (324 mg, 1.0 mmol) in thiophene ethanol (2.3 mL, 20.4 mmol) was stirred under microwave irradiations (100 W) at 110° C. for 30 minutes. The reaction mixture was then partitioned between dichloromethane (20 mL) and a solution of sodium hydroxyde (1N, 10 mL). The aqueous layer was separated and extracted with dichloromethane (2×10 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, using petroleum ether/ethyl acetate (85:15) as eluent. The title product was obtained as a yellow solid (210 mg, 59%).

Aufarbeitung

  1. customThe reaction mixture was then partitioned between dichloromethane (20 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane (2×10 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2054d7a1c1aa4ecc9207d1f1402d14fa
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051321B2

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