Sulfuric Acid → Isoxanthohumol

HRID 564214

반응식

HRID 564214 반응식
C=CCO[C@H](C1C2C(=CC=CC=2)N=CC=1)[C@H]1[N+]2(CC3C4C(=CC=CC=4)C=C4C=3C=CC=C4)C[C@H](C=C)[C@@H](CC2)C1.[Br-].[CH3:42][C:43]([CH3:67])=[CH:44][CH2:45][C:46]1[C:47]([OH:66])=[CH:48][C:49]([O:64][CH3:65])=[C:50]([C:53](/[CH:55]=[CH:56]/[C:57]2[CH:58]=[CH:59][C:60]([OH:63])=[CH:61][CH:62]=2)=[O:54])[C:51]=1[OH:52].[OH-].[Na+].OS(O)(=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:42][C:43]([CH3:67])=[CH:44][CH2:45][C:46]1[C:47]([OH:66])=[CH:48][C:49]([O:64][CH3:65])=[C:50]2[C:53](=[O:54])[CH2:55][CH:56]([C:57]3[CH:58]=[CH:59][C:60]([OH:63])=[CH:61][CH:62]=3)[O:52][C:51]=12

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 639665XanthohumolHCID 10886583O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide

생성물 1

HCID 513197Isoxanthohumol

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 8857Ethyl Acetate용매

실험 절차

To the suspension of the O'Donnell phase transfer catalyst O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (34 mg, 0.056 mmol) in 1 ml of toluene is added xanthohumol (2 OH groups protected) (in part TIPS-protected: 37 mg, 0.056 mmol) in 1 ml of toluene. Subsequently, 0.5 ml of 25% NaOH is added and the mixture is stirred for 24 h at room temperature. For workup, 20 ml of H2O and 20 ml of ethyl acetate are added. The aqueous phase is acidified with H2SO4 and extracted twice with ethyl acetate. The organic phase is washed with NH4Cl solution and H2O, dried and eluted through a silica gel column using CHCl3/methanol. Removal of protection proceeds in a manner known from the literature.

후처리

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phase is washed with NH4Cl solution and H2O
  3. customdried
  4. washeluted through a silica gel column
  5. customRemoval of protection proceeds in a manner

출처 및 근거

ORD 기록
ord-8414655f00644a008ccf2d4329be30ca
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067622B2

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