Water → HCID 23726708, compound

HRID 884378Notes

Reaction equation

HRID 884378 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]=[CH2:14])[C@H:9]1[CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O.OS(O)(=O)=O.O>CC(C)=O.C(O)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]=[CH2:14])[C@H:9]1[C:15]([OH:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 23726640HCID 23726640, compoundHCID 131709961Jones' reagent

Product 1

HCID 23726708HCID 23726708, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

600 mg of alcohol 165 (2.64 mmol) was dissolved in 15 ml of acetone, cooled to 0° C. and added dropwise with 5 ml of Jones reagent (7.40 mmol, 2.8 eq.) (freshly prepared from 2 g of CrO3, 2.7 g of conc. H2SO4, 12 ml of H2O) and stirred for 2 h at RT, the course of the reaction being monitored using TLC (EE/CH 1:1). This was followed by addition of 4 ml of isopropanol, during which the orange color of the reaction mixture gradually turned green-brown. Filtration over Celite was followed by washing with 5 ml of an acetone/glacial acetic acid mixture (20:1) and concentrating to dryness. The remaining greenish residue was purified using silica gel column chromatography (CH2Cl2/MeOH 20:1), thereby obtaining 470 mg of vinylproline 166 (1.95 mmol, 74%) in the form of white crystals suitable for X-ray crystallographic analysis.

Workup

  1. filtrationFiltration over Celite
  2. washby washing with 5 ml of an acetone/glacial acetic acid mixture (20:1)
  3. concentrationconcentrating to dryness
  4. customThe remaining greenish residue was purified

Sources & evidence

ORD record
ord-6eefcebd1dd440369082ad5bda7a043f
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

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