Hydrochloric Acid → (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

HRID 1009163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009163
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.CSC.B.C1COCC1.[Br:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[O:38][C:37]([CH3:46])([C:42]([F:45])([F:44])[F:43])[CH2:36][C:35]2=[O:47].Cl>C1(C)C=CC=CC=1>[Br:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[O:38][C:37]([CH3:46])([C:42]([F:43])([F:45])[F:44])[CH2:36][C@H:35]2[OH:47]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 12423031(Dimethyl sulfide)trihydroboronHCID 673056026-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

Produkt 1

HCID 67305384(4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a cooled (ice bath) solution of (s)-2-methyl-cbs-oxazaborolidine 1.0 M in toluene (100 μl, 100 μmol) was added borane-dimethyl sulfide 2.0 M in THF (500 μl, 1000 μmol). After stirred 15 min, a solution of 6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-one (309 mg, 1000 μmol) in toluene was added drop wise. The reaction was completed after stirring 9 h at 0° C. 2N HCl was added slowly to quench the reaction. The resulted mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column to afford the title compound.

Aufarbeitung

  1. stirringafter stirring 9 h at 0° C
  2. customto quench
  3. customthe reaction
  4. extractionThe resulted mixture was extracted with EtOAc
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-2396bf1544d14e289ddb24fecf91e9d5
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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