Sodium Acetate → 226414-39-7

HRID 617692Notes

Reaction equation

HRID 617692 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C@@H:5]([OH:10])[C@@H:6]([CH3:9])[CH2:7][CH3:8])[CH3:2].CC([O-])=O.[Na+].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:11])[C:5](=[O:10])[C@@H:6]([CH3:9])[CH2:7][CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 13026601HCID 13026601, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 18391773226414-39-7Yield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+)-hydroxy ester [3] (2.0 g, 12.5 mmol) in 20 ml of CH2Cl2 at room temperature were added successively NaOAc (312 mg, 3.8 mmol) and PCC (pyridinium chlorochromate, 4.04 g, 18.75 mmol). After 24 h at room temperature, the conversion was only 60% and 2.02 g PCC were re-added. The mixture was stirred 96 h at room temperature, rapidly filtered on SiO2, concentrated and purified by flash chromatography on SiO2 to give 1.58 g of ester [4]. At this stage, a GC control on chiral column (CHIRASIL-DEX CB, 25 m×0.25 mm, isoth. 80°) showed a purity of 100% and an ee (enantiomeric excess) of 100%. After bulb-to-bulb distillation (Eb=100°, 16 mbars), 1.51 g (yield: 76.3%) of pure (+)-ester [4] were obtained.

Workup

  1. additionwere re-added
  2. filtrationrapidly filtered on SiO2
  3. concentrationconcentrated
  4. custompurified by flash chromatography on SiO2

Sources & evidence

ORD record
ord-9198397c0ad34fb7ad5b29acbac48cdd
Source dataset
uspto-grants-1999_09
Patent number
US05952292

Reaction notes

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