Pyridine → 2,4,4'-Trihydroxydeoxybenzoin

HRID 1760763

반응식

HRID 1760763 반응식
FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1.[OH:20][C:21]1(C(F)(F)F)[C:26]2[CH:27]=[CH:28][C:29]([OH:31])=[CH:30][C:25]=2[O:24]C(C2C=CC(OCCN3CCCCC3)=CC=2)[CH:22]1[C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:24][C:25]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:26]=1[C:21](=[O:20])[CH2:22][C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 155474944,7-dihydroxy-3-(4-hydroxyphenyl)-2-[4-(2-piperidin-1-ylethoxy)-phenyl]-4-(trifluoromethyl)-2,3-dihydro-4H-1-benzopyran

생성물 1

HCID 6400962,4,4'-Trihydroxydeoxybenzoin

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

0.88 ml of trifluoroacetic acid anhydride and 1.37 ml of pyridine are simultaneously added in drops to 1.15 g of 4,7-dihydroxy-3-(4-hydroxyphenyl)-2-[4-(2-piperidin-1-ylethoxy) -phenyl]-4-(trifluoromethyl)-2,3-dihydro-4H-1-benzopyran in 20 ml of THF. It is stirred for 4 hours at room temperature before 70 ml of ethyl acetate and 20 ml of 10% sodium carbonate solution are added. It is stirred for 20 more minutes at room temperature. The phases are separated, and the aqueous phase is shaken out three times with 40 ml of ethyl acetate. The combined organic phases are washed twice with 20 ml of water, dried on magnesium sulfate and concentrated by evaporation. The product is prepurified on silica gel with dichloromethane/methanol and then purified with HPLC (nucleosil 50-7, dichloromethane/methanol 85:15, 40 ml/min). 590 mg is obtained.

후처리

  1. additionare added
  2. customThe phases are separated
  3. stirringthe aqueous phase is shaken out three times with 40 ml of ethyl acetate
  4. washThe combined organic phases are washed twice with 20 ml of water
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. custompurified with HPLC (nucleosil 50-7, dichloromethane/methanol 85:15, 40 ml/min)
  8. custom590 mg is obtained

출처 및 근거

ORD 기록
ord-f1614aa6f5ea4a6ea4c7928fb712567a
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844336B2

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