Ammonium Chloride → (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol

HRID 1195482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195482
C(O[CH2:5]/[CH:6]=[C:7](\[CH3:21])/[CH2:8][CH2:9][C:10]1[C:15]([CH3:16])=[C:14]([OH:17])[C:13]([CH3:18])=[C:12]([CH3:19])[C:11]=1[OH:20])(=O)C.[H-].[Ca+2].[H-].[Cl-].[NH4+]>CS(C)=O>[CH3:21][C@@:7]1([CH:6]=[CH2:5])[CH2:8][CH2:9][C:10]2[C:15]([CH3:16])=[C:14]([OH:17])[C:13]([CH3:18])=[C:12]([CH3:19])[C:11]=2[O:20]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 3033859Calcium hydrideHCID 19819049(E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate

Produkt 1

HCID 22843764(S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-olAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 106 mg (0.36 mmol) of (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate and 9 mg (3%) of [[(R)-6,6'-dimethyl-1,1'-biphenyl-2,2'-bis(diphenylphosphine)]-P,P'][(η-3)-2-propenyl]palladium perchlorate in 2 ml of DMSO was treated with 15 mg of calcium hydride and stirred at room temperature for three days. Thereafter, the mixture was poured into saturated ammonium chloride solution and extracted with ether. The combined extracts were washed with water and dried. The residue remaining after removal of the solvent was purified as described in Experiment 1, yielding 56 mg of (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol. O.P. 33%.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe combined extracts were washed with water
  3. customdried
  4. customafter removal of the solvent
  5. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-c164f9981cbf4bf89597af5800d473d6
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05110955

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