(Z)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate → (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol

HRID 1195480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195480
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>CS(C)=O.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

4

Edukt 1

HCID 86745750(Z)-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 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 125 mg (0.43 mmol) of (Z)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate, 8 mg (3%) of (S)-2,2'-bis-(diphenylphosphino)-1,1'-binaphthalene and 2.3 mg (1.5%) of π-allylpalladium chloride dimer in DMSO (3 ml) was left at 60° C. for 17 hours. After cooling the mixture was diluted with water and extracted with ether. The extracts were washed with water, dried, concentrated and the residue was purified as in Experiment 1, yielding 86 mg of (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol. O.P. 36%.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified as in Experiment 1

Quellen und Nachweise

ORD-Eintrag
ord-331d439b3ade4588b4a4e5069a25e3c4
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05110955

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