Sodium Acetate → ethyl 2-((4R,6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

HRID 877942Notes

Reaction equation

HRID 877942 reaction equation
Cl[CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4]1.[C:17]([O-:20])(=[O:19])[CH3:18].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:17]([O:20][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4]1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 67323517ethyl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Product 1

HCID 53339171ethyl 2-((4R,6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
27.5 °C

Procedure

Mixture of ethyl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (60 grams), tetra butyl ammonium bromide (79 grams) and anhydrous sodium acetate (61.2 grams) was heated to reflux temperature and stirred. After the completion of the reaction, the reaction mixture was cooled to 25-30° C. and petroleum ether (50 ml) was added to it then stirred for 60 minutes at 25-30° C. The reaction mixture was filtered and washed with petroleum ether. The solvent from the filtrate was distilled off under reduced pressure to get the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature
  3. customAfter the completion of the reaction
  4. stirringthen stirred for 60 minutes at 25-30° C
  5. filtrationThe reaction mixture was filtered
  6. washwashed with petroleum ether
  7. distillationThe solvent from the filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-39710b81b78c4c13afa29ee5dc0b9e9e
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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