Tetrahydrofuran → HCID 22616786, compound

HRID 843190Notes

Reaction equation

HRID 843190 reaction equation
[CH:1]12C[CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([CH:10]([C:14]([OH:16])=[O:15])[C:11]([OH:13])=[O:12])=O.C12CCC(C=C1)CC2[CH:25]=[O:26].O1CCC[CH2:28]1>>[CH:2]12[CH2:1][CH2:6][CH:5]([CH:4]=[CH:3]1)[CH2:28][CH:8]2[C:10]([CH2:25][OH:26])([C:14]([OH:16])=[O:15])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 12493694Bicyclo[2.2.2]oct-5-ene-2-carbaldehydeHCID 22616800HCID 22616800, compound

Product 1

HCID 22616786HCID 22616786, compoundYield 120.8%

Procedure

To a solution containing sodium malonate (17.0 g) of Example 7 in dry tetrahydrofuran (100 g), bicyclo[2,2,2]oct-5-ene-2-carboxaldehyde (13.6 g) obtained in Preparation Example 5 is slowly added, and the reaction is carried out at −20° C. in a nitrogen atmosphere for 1 hour, and then at 50° C. for 10 hours. Then, the reaction mixture is worked up as in the procedure of Example 1, to obtain 22 g of the pure title compound (purity: 99%, yield: 92%).

Workup

  1. customobtained in Preparation Example 5
  2. additionis slowly added
  3. waitat 50° C. for 10 hours

Sources & evidence

ORD record
ord-70ae434e77464a1ebae14c028eeb5e8e
Source dataset
uspto-grants-2002_04
Patent number
US06376632B1

Reaction notes

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