Hydrochloric Acid → HCID 67283612, compound

HRID 407863Notes

Reaction equation

HRID 407863 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 67283612HCID 67283612, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b1acda267b2347afb94038d8b77de9a4
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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