Dimethylformamide → HCID 20768134, Verbindung

HRID 985036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985036
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:4][C:3]=1[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>O>[C:34]([O:33][C:31](=[O:32])[CH2:30][O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:4][C:3]=1[CH3:17])([CH3:37])([CH3:36])[CH3:35]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 618879Bis(4-hydroxy-3-methylphenyl) Sulfide

Produkt 1

HCID 20768134HCID 20768134, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

An oven-dried 100 mL round-bottomed flask was charged with bis-(4-hydroxy-3-methylphenyl)-sulfide (8.6 g, 34.9 mmol), finely powdered Cs2CO3 (11.9 g, 36.7 mmol), and anhydrous DMF (35 mL). Next, tert-butyl bromoacetate (5.2 mL, 34.9 mmol, Aldrich) was added dropwise, and the reaction was stirred vigorously overnight at room temperature. The reaction was poured into 500 mL of water and extracted with 3×50 mL of methylene chloride. The combined organics were washed with 2×150 mL of water, dried over Na2SO4, and concentrated to a slightly yellow oil. The mixture was then purified by flash chromatography (SiO2 gel 60, eluted with 10% hexanes in DCM—5% hexanes in DCM—100% DCM). The fractions containing only desired product 1.1 were combined and concentrated to a white solid (3.5 g). The mixed fractions were combined, concentrated, and resubjected to the same chromatography conditions to yield an additional 2.0 g of pure 1.1. 1H NMR (400 MHz) (CDCl3) δ 7.13 (2H, m); 7.06 (2H, m); 6.70 (1H, d, J=8.3 Hz); 6.59 (1H, d, J=8.4 Hz); 4.50 (2H, s); 2.23 (3H, s); 2.20 (3H, s); 1.48 (9H, s).

Aufarbeitung

  1. extractionextracted with 3×50 mL of methylene chloride
  2. washThe combined organics were washed with 2×150 mL of water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a slightly yellow oil
  5. customThe mixture was then purified by flash chromatography (SiO2 gel 60, eluted with 10% hexanes in DCM—5% hexanes in DCM—100% DCM)
  6. additionThe fractions containing only desired product 1.1
  7. concentrationconcentrated to a white solid (3.5 g)
  8. concentrationconcentrated
  9. customto yield an additional 2.0 g of pure 1.1

Quellen und Nachweise

ORD-Eintrag
ord-11fadcaef7e24419a02330e257caeb34
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869975B2

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