Hydrochloric Acid → HCID 67777371, compound

HRID 1430744Notes

Reaction equation

HRID 1430744 reaction equation
[CH:1]12[O:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[CH:2]2[C:3](=[O:12])[CH2:4][C:5]1=[O:11].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:39][C:40]1[CH:53]=[CH:52][C:43]([C:44]2[CH:45]=[CH:46][C:47]([CH3:51])=[C:48]([Pb+3])[CH:49]=2)=[CH:42][CH:41]=1.Cl>C(OCC)(=O)C.C1(C)C=CC=CC=1>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([C:44]2[CH:45]=[CH:46][C:47]([CH3:51])=[C:48]([CH:4]3[C:3](=[O:12])[CH:2]4[CH:6]([CH:7]5[O:10][CH:1]4[CH:9]=[CH:8]5)[C:5]3=[O:11])[CH:49]=2)=[CH:52][CH:53]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 2067932010-Oxa-tricyclo[5.2.1.0*2,6*]dec-8-ene-3,5-dioneHCID 178476525HCID 178476525, compound

Product 1

HCID 67777371HCID 67777371, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (374 mg, 2.3 mmol) and phenanthroline (610 mg, 5 mmol) under an atmosphere of nitrogen is added dry toluene (20 ml) and 4′-chloro-4-methylbiphen-3-yllead triacetate (2.0 g, 3.4 mmol). The reaction mixture is heated at reflux for 3.5 hours, then cooled to room temperature, acidified to pH1 with 2N aqueous hydrochloric acid (20 ml), ethyl acetate (20 ml) added and the mixture is filtered to remove solids. The filtrate is poured into a separating funnel and extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The crude product is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(4′-chloro-4-methylbiphenyl-3-yl)-10-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3.5 hours
  3. additionadded
  4. filtrationthe mixture is filtered
  5. customto remove solids
  6. additionThe filtrate is poured into a separating funnel
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate is evaporated under reduced pressure
  11. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4cf0a6eea0cf423781420c1640f7e618
Source dataset
uspto-grants-2015_01
Patent number
US08940913B2

Reaction notes

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