Water → tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one

HRID 6058

Reaction equation

HRID 6058 reaction equation
[CH2:1]([C@@H:7]1[CH:12]([OH:13])[CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[CH2:1]([C@@H:7]1[C:12](=[O:13])[CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 67855756tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-oneHCID 131709961Jones' reagent

Product 1

HCID 67855749tetrahydro-3-hexyl-4-oxo-(R)-6-undecyl-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. customdid not exceed 25° C
  2. customThe lactone precipitated out
  3. filtrationwas filtered off
  4. customAfter recrystallization in ether/n-hexane there

Sources & evidence

ORD record
ord-518a16e34f3943a5b14400a699394dc9
Source dataset
uspto-grants-1993_09
Patent number
US05246960

Linked notes

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