Hydrochloric Acid → (1RS,2SR,6RS,7SR)-4-(4-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

HRID 407863노트

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HRID 407863 반응식
C1(C)C=CC=CC=1.[CH:8]12[O:17][CH:14]([CH2:15][CH2:16]1)[CH:13]1[CH:9]2[C:10](=[O:19])[CH2:11][C:12]1=[O:18].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:32][C:33]1[CH:38]=[CH:37][C:36]([Pb+3])=[C:35]([CH2:40][CH3:41])[CH:34]=1.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Br:32][C:33]1[CH:38]=[CH:37][C:36]([CH:11]2[C:10](=[O:19])[CH:9]3[CH:13]([CH:14]4[O:17][CH:8]3[CH2:16][CH2:15]4)[C:12]2=[O:18])=[C:35]([CH2:40][CH3:41])[CH:34]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 5935195110-Oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dioneHCID 178476529HCID 178476529, 화합물

생성물 1

HCID 67283612(1RS,2SR,6RS,7SR)-4-(4-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매

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온도
80 °C

실험 절차

4-Dimethylaminopyridine (3.67 g, 30.0 mmol) and toluene (10 ml) are added to a solution of (1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione (1.0 g, 6.0 mmol) in chloroform (40 ml) and the reaction mixture is heated to 80° C. 4-Bromo-2-ethylphenyllead triacetate (5.13 g, 9.04 mmol) is added portionwise over 20 minutes, and once the addition is complete the reaction mixture is stirred at 80° C. for a further 4 hours. The mixture is cooled to room temperature, 2 M aqueous hydrochloric acid (40 ml) is added, and the mixture is stirred vigorously for 15 minutes, then filtered through a small plug of diatomaceous earth, washing with 40 ml dichloromethane. The organic phase is separated, and the aqueous phase is extracted with dichloromethane (2×20 ml). The organic solutions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(4-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

후처리

  1. additiononce the addition
  2. temperatureThe mixture is cooled to room temperature
  3. stirringthe mixture is stirred vigorously for 15 minutes
  4. filtrationfiltered through a small plug of diatomaceous earth
  5. washwashing with 40 ml dichloromethane
  6. customThe organic phase is separated
  7. extractionthe aqueous phase is extracted with dichloromethane (2×20 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-b1acda267b2347afb94038d8b77de9a4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754242B2

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