Methyl iodide → Methyl 2-(1-(4-bromophenyl)cyclopentyloxy)acetate

HRID 885120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885120
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.IC.[C:20](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:13][CH2:14][C:15]([O:17][CH3:20])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 687203352-(1-(4-Bromophenyl)cyclopentyloxy)acetic acid

Produkt 1

HCID 68721066Methyl 2-(1-(4-bromophenyl)cyclopentyloxy)acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To an ambient solution of Example 30B (200 mg, 0.668 mmol) in N,N-dimethylformamide (4 mL) was added iodomethane (0.208 mL, 3.34 mmol) and potassium carbonate (184 mg, 1.34 mmol). The mixture was stirred at room temperature for 40 h, and then diluted with water (10 mL) and ethyl acetate (20 mL). The layers were separated, and the organic was washed with water (3×10 mL), brine (1×10 mL), dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.67-1.72 (m, 2H), 1.74-1.84 (m, 4H), 2.10 (m, 2H), 3.58 (s, 3H), 3.67-3.70 (m, 2H), 7.34-7.40 (m, 2H), 7.51-7.57 (m, 2H).

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic was washed with water (3×10 mL), brine (1×10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-de3f54d0309e488da01bedddc0e78000
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242139B2

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