Hydrochloric Acid → HCID 68487113, 화합물

HRID 1191546노트

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HRID 1191546 반응식
C(Cl)(Cl)Cl.[CH3:5][C@@:6]12[O:13][C@@H:10]([CH2:11][CH2:12]1)[C:9](=[O:14])[CH2:8][C:7]2=[O:15].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][CH3:42])=[C:37]([Pb+3])[CH:36]=2)=[CH:31][CH:30]=1.Cl>C1(C)C=CC=CC=1>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][CH3:42])=[C:37]([CH:8]3[C:9](=[O:14])[C@H:10]4[O:13][C@:6]([CH3:5])([CH2:12][CH2:11]4)[C:7]3=[O:15])[CH:36]=2)=[CH:33][CH:34]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 67533518(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dioneHCID 178476534HCID 178476534, 화합물

생성물 1

HCID 68487113HCID 68487113, 화합물수율 67.8%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a mixture of chloroform (2.0 ml) and toluene (0.5 ml) is added (1R*,5S*)-1-methyl-8-oxa-bicyclo[3.2.1]octane-2,4-dione (0.10 g, 0.6 mmol) and N,N-dimethylamino-pyridine (0.395 g, 3.2 mmol) under a nitrogen atmosphere with stirring. To this reaction mixture is added 4′-chloro-4-ethylbiphenyl-3-yllead triacetate (0.42 g, 0.70 mmol) in one portion, then the mixture is heated at 80° C. for 1-2 hours. The reaction mixture is cooled to room temperature, acidified with dilute aqueous hydrochloric acid then filtered through diatomaceous earth to remove inorganic residues (subsequent washing with dichloromethane). The aqueous fractions are extracted with dichloromethane (2×5 ml), all organic fractions are combined, dried over sodium sulfate then concentrated under vacuum to give the crude product which is purified by flash chromatography (hexane/ethyl acetate) to give (1R*,5S*)-3-(4′-chloro-4-ethylbiphenyl-3-yl)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione (0.150 g) as a white solid.

후처리

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationthen filtered through diatomaceous earth
  3. customto remove inorganic
  4. washresidues (subsequent washing with dichloromethane)
  5. extractionThe aqueous fractions are extracted with dichloromethane (2×5 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationthen concentrated under vacuum
  8. customto give the crude product which
  9. customis purified by flash chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-766603ceb24f4ef6af6958fa51292acb
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680012B2

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