Hydrochloric Acid → HCID 75288490, compound

HRID 1430751Notes

Reaction equation

HRID 1430751 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].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:25][C:26]1[CH:40]=[CH:39][C:29]([C:30]2[CH:31]=[CH:32][C:33]([CH2:37][CH3:38])=[C:34]([Pb+3])[CH:35]=2)=[CH:28][CH:27]=1.C(Cl)(Cl)Cl.Cl>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:25][C:26]1[CH:40]=[CH:39][C:29]([C:30]2[CH:35]=[CH:34][C:33]([CH2:37][CH3:38])=[C:32]([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:31]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 2067932010-Oxa-tricyclo[5.2.1.0*2,6*]dec-8-ene-3,5-dioneHCID 178476534HCID 178476534, compound

Product 1

HCID 75288490HCID 75288490, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of (1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (1.7 g, 0.01 mol), 4-dimethylaminopyridine (5.0 g, 0.04 mol) and 4′-chloro-4-ethylbiphen-3-yllead triacetate (9.2 g, 0.015 mol) under an atmosphere of nitrogen is added dry chloroform (50 ml)). The reaction mixture is heated at 40° C. for 5 hours, then cooled to room temperature. The mixture is diluted with ethyl acetate (50 ml), acidified with 2N aqueous hydrochloric acid (50 ml), 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-ethylbiphen-3-yl)-10-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe mixture is filtered
  3. customto remove solids
  4. additionThe filtrate is poured into a separating funnel
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dacd2030ac6149f7b132a0e0216b196a
Source dataset
uspto-grants-2015_01
Patent number
US08940913B2

Reaction notes

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