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Propargyl bromide → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-prop-2-yn-1-yl-1,3-oxazolidin-2-one

HRID 604653
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 604653
[H-].[Na+].[F:3][C:4]([F:23])([F:22])[C:5]1[CH:6]=[C:7]([C@H:15]2[O:19][C:18](=[O:20])[NH:17][C@H:16]2[CH3:21])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.[CH2:24](Br)[C:25]#[CH:26].[NH4+].[Cl-]>C1COCC1>[F:23][C:4]([F:3])([F:22])[C:5]1[CH:6]=[C:7]([C@H:15]2[O:19][C:18](=[O:20])[N:17]([CH2:26][C:25]#[CH:24])[C@H:16]2[CH3:21])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1
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Komponenten

6

Edukt 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one

Produkt 1

HCID 86627632(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-prop-2-yn-1-yl-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (192 mg, 60% dispersion in mineral oil, 4.79 mmol) was added to a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (1.00 g, 3.19 mmol) in dry THF (30 mL) at room temperature under N2. After stirring for 30 min at room temperature, propargyl bromide (80 wt % solution in toluene, 712 μL, 570 mg, 4.17 mmol) was added. The reaction mixture was stirred overnight at room temperature. Saturated NH4Cl (20 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 40×160 mm, 0-40% EtOAc in hexanes gradient) to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-prop-2-yn-1-yl-1,3-oxazolidin-2-one. Rf=0.31 (20% EtOAc/hexanes). LCMS calc.=352.1; found=352.1 (M+1)+. 1H NMR (600 MHz, CDCl3): δ 7.88 (s, 1H); 7.76 (s, 2H); 5-74 (d, J=8.2 Hz, 1H); 4.454-39 (m, 2H); 3.81 (dd, J=2.5, 17.8 Hz, 1H); 2.33 (t, J=2.5 Hz, 1H); 0.84 (d, J=6.6 Hz, 4H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThis was purified by flash chromatography (Si, 40×160 mm, 0-40% EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d9f003a8daec4bc5b578e5966e173f27
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07910592B2

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