cis,cis-1,5-Cyclooctadiene → HCID 89597150, compound

HRID 536910Notes

Reaction equation

HRID 536910 reaction equation
[CH:1]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.[N+](=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>C(Cl)Cl>[C@H:1]12[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C@H:8]1[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 8135cis,cis-1,5-CyclooctadieneHCID 3296813HCID 3296813, compound

Product 1

HCID 89597150HCID 89597150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,5-cyclooctadiene (5.27 mL, 43.0 mmol) and Rh2(OAc)4 (100 mg, 0.23 mmol) in CH2Cl2 (5 mL) was added dropwise in 3 h a solution of diethyl diazomalonate (1.0 g, 5.37 mmol) in CH2Cl2 (5 mL). This solution was stirred for 24 h at rt. The CH2Cl2 was evaporated and the excess of cyclooctadiene was removed by filtration over a glass filter filled with silica (cluens: heptane). The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (EtOAc:heptane, 1:10) to afford IIa.8 (1.03 g, 72%).

Workup

  1. customThe CH2Cl2 was evaporated
  2. customthe excess of cyclooctadiene was removed by filtration over a glass
  3. filtrationfilter
  4. additionfilled with silica (cluens: heptane)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (EtOAc:heptane, 1:10)
  7. customto afford IIa.8 (1.03 g, 72%)

Sources & evidence

ORD record
ord-a730ee8367de49bea364c58bf4ddefca
Source dataset
uspto-grants-2014_10
Patent number
US08859629B2

Reaction notes

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