Allyltributylstannane → 5-allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one

HRID 586781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586781
[CH3:1][C:2]1([CH3:20])[O:7][C:6](=[O:8])[C:5]2[C:9](S(C(F)(F)F)(=O)=O)=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1.[Li+].[Cl-].[CH2:23]([Sn](CCCC)(CCCC)CCCC)[CH:24]=[CH2:25].[F-].[K+]>CC1CNC(=O)C1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[CH2:25]([C:9]1[C:5]2[C:6](=[O:8])[O:7][C:2]([CH3:20])([CH3:1])[O:3][C:4]=2[CH:12]=[CH:11][CH:10]=1)[CH:24]=[CH2:23]

Komponenten

8

Edukt 4

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 22336191HCID 22336191, Verbindung

Produkt 1

HCID 111486725-allyl-2,2-dimethyl-benzo[1,3]dioxin-4-oneAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 521585Tris(furan-2-yl)phosphaneKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 5339204-Methyl-2-pyrrolidinoneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 2,2-dimethyl-5-(trifluoromethanesulfonyl)-benzo[1,3]dioxin-4-one (iii) (2.0 g, 6.13 mmol), anhydrous LiCl (0.8 g, 18.4 mmol), Pd2(dba)3 (112 mg, 0.12 mmol), and tri-(2-furyl)phosphine (115 mg, 0.49 mmol) in 4-methyl-2-pyrrolidinone (10 mL) was added allyltributyltin (2.35 mL, 7.36 mmol). After stirring for 48 h at rt, saturated aqueous KF (20 mL) was added and an extraction was performed with Et2O (3×). The combined organics were dried over MgSO4, concentrated in vacuo and the residue was purified by FC (4% EtOAc/hexanes) to give 1.3 g of 5-allyl-2,2-dimethyl-benzo[1,3]dioxin-4-one (iv) which was slightly impure.

Aufarbeitung

  1. extractionan extraction
  2. dry with materialThe combined organics were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by FC (4% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8133c88ed9e448fd85155daefa4867d4
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936723B2

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