Valtrate → Baldrinal

HRID 2060651Notes

Reaction equation

HRID 2060651 reaction equation
CC(CC(O[C@@H:8]1[C@@:12]2([O:14][CH2:13]2)[C@H:11]2[C@H:15](OC(CC(C)C)=O)[O:16][CH:17]=[C:18]([CH2:19][O:20][C:21]([CH3:23])=[O:22])[C:10]2=[CH:9]1)=O)C>C(Cl)(Cl)Cl.FC(F)(F)C(O)=O>[CH3:23][C:21]([O:20][CH2:19][C:18]1[C:10]2=[CH:9][CH:8]=[C:12]([CH:13]=[O:14])[C:11]2=[CH:15][O:16][CH:17]=1)=[O:22]

Participants

4

Reactant 1

HCID 442436Valtrate

Product 1

HCID 159846Baldrinal

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent3×HCID 6422Trifluoroacetic acidSolvent

Procedure

Valtrate (1) (9.2 g) was dissolved in 20 ml of chloroform at room temperature. In another flask, 20 g of trifluoroacetic acid was dissolved in 40 ml of chloroform. This second solution then was added to the first solution. The clear solution became dark green/blue after stirring for 5 minutes. Chloroform (60 ml) was added to the reaction mixture, and the reaction mixture was washed with water until a pH of 4 was reached. Sodium chloride with 0.5% NaHCO3 (125 mL) was added to neutralize the mixture. Baldrinal (2, 1.1 g) was collected as a yellow liquid using column chromatography with 8:2 hexanes:ethyl acetate as solvent.

Workup

  1. additionThis second solution then was added to the first solution
  2. washthe reaction mixture was washed with water until a pH of 4
  3. additionSodium chloride with 0.5% NaHCO3 (125 mL) was added
  4. customBaldrinal (2, 1.1 g) was collected as a yellow liquid

Sources & evidence

ORD record
ord-dc7d2566176748e1af3e9714dba47539
Source dataset
uspto-grants-2012_10
Patent number
US08278451B2

Reaction notes

Loading…