Tetrahydrofuran → HCID 22616785, compound

HRID 843191Notes

Reaction equation

HRID 843191 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.C12C=CC(CC1)CCC2[CH:26]=[O:27].O1CC[CH2:30][CH2:29]1>>[CH:2]12[CH:1]=[CH:6][CH:5]([CH2:4][CH2:3]1)[CH2:30][CH2:29][CH:8]2[C:10]([CH2:26][OH:27])([C:14]([OH:16])=[O:15])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 22616781HCID 22616781, compoundHCID 22616800HCID 22616800, compound

Product 1

HCID 22616785HCID 22616785, compoundYield 124.5%

Procedure

To a solution containing sodium malonate (17.0 g) of Example 7 in dry tetrahydrofuran (100 g), bicyclo[3,2,2]non-8-ene-2-carboxaldehyde (15 g) obtained in Preparation Example 6 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 24 g of the pure title compound (purity: 99%, yield: 90%).

Workup

  1. customobtained in Preparation Example 6
  2. additionis slowly added
  3. waitat 50° C. for 10 hours

Sources & evidence

ORD record
ord-a951c593cb964236b5f9ada8f144a4b1
Source dataset
uspto-grants-2002_04
Patent number
US06376632B1

Reaction notes

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