Pyridine → HCID 57444524, compound

HRID 2250551Notes

Reaction equation

HRID 2250551 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.N1C=CC=CC=1.[CH3:17][O:18][CH2:19][C:20](Cl)=[O:21]>ClCCl>[CH3:17][O:18][CH2:19][C:20]([CH:6]1[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:5])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 96623Methoxyacetyl chloride

Product 1

HCID 57444524HCID 57444524, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Meldrum's acid (30 g, 0.208 mol) in dichloromethane (420 mL) was added pyridine (33.7 mL, 0.416 mol) over 3 minutes in an ice-methanol bath under nitrogen atmosphere (−9° C.). To this mixture was added dropwise a solution of methoxyacetyl chloride (24.8 g) in dichloromethane (180 mL) over 1 hour period at the temperature. After addition, the reaction mixture was stirred at the temperature for 1 hour and at ambient temperature for 2 hours. The mixture was quenched with 1N hydrochoric acid (600 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give 5-(methoxyacetyl)-2,2-dimethyl-1,3-dioxane-4,6-dione as dark orange oil (38.1 g, 84.7%).

Workup

  1. additionAfter addition
  2. customThe mixture was quenched with 1N hydrochoric acid (600 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-e6d19b8ce95e457f96b2efcd72cb8c7b
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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