Reaction #6154

ord-518a16e34f3943a5b14400a699394dc9

Reaction equation

O
H2O
CCCCCCCCCCCC1CC(O)[C@@H](CCCCCC)C(=O)O1
tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones' reagent
→
CCCCCCCCCCCC1CC(=O)[C@@H](CCCCCC)C(=O)O1
tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one

Reactants

O
H2O
—
diastereomer mixture
CCCCCCCCCCCC1CC(O)[C@@H](CCCCCC)C(=O)O1
tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones' reagent

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherdid not exceed 25° C
  2. 2
    OtherThe lactone precipitated out
  3. 3
    Filtrationwas filtered off
  4. 4
    OtherAfter recrystallization in ether/n-hexane there

Procedure

M)b) 3 g of a diastereomer mixture of tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one were dissolved in 300 ml of acetone. 3 ml of Jones' reagent were added dropwise while stirring in such a manner that the temperature did not exceed 25° C. After 3 hours the reaction mixture was poured into 700 ml of H2O. The lactone precipitated out and was filtered off. After recrystallization in ether/n-hexane there were obtained 1.7 g of tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one, m.p. 112.5°-113.5° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246960uspto-grants-1993_09