Carbon tetrabromide → 6-(3-Bromomethyl-pent-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

HRID 272203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272203
[CH2:1]([C:3]1[C:4]([CH3:27])=[C:5]2[C:9](=[C:10]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=1[CH2:12][CH:13]=[C:14]([CH2:17]O)[CH2:15][CH3:16])[C:8](=[O:26])[O:7][CH2:6]2)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:48]>C(Cl)Cl>[Br:48][CH2:17][C:14]([CH2:15][CH3:16])=[CH:13][CH2:12][C:11]1[C:10]([O:19][CH2:20][CH2:21][Si:22]([CH3:23])([CH3:25])[CH3:24])=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:26])=[C:4]([CH3:27])[C:3]=1[CH2:1][CH3:2]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 670102685-Ethyl-6-(3-hydroxymethyl-pent-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

Produkt 1

HCID 670103606-(3-Bromomethyl-pent-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-oneAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Ethyl-6-(3-hydroxymethyl-pent-2-enyl)-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (35.4 mg, 0.090 mmol) was dissolved in DCM (3.0 mL). Polymer-bound triphenylphosphine (3 mmol/g, 90.7 mg) was added, and the mixture was mechanically stirred at room temperature. Carbon tetrabromide (90.2 mg, 0.272 mmol) was added and the solution was stirred at room temperature. After 2 hours, the reaction was filtered and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography to provide 32.0 mg (78%) of the desired product. The material was used in the next step without further characterization.

Aufarbeitung

  1. stirringthe solution was stirred at room temperature
  2. filtrationthe reaction was filtered
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ffc67dff0544144bba053c409313d73
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452901B2

Notizen zur Reaktion

Wird geladen…