Hydrochloric Acid → 2-(1,3-Dioxolan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate

HRID 2253574Notes

Reaction equation

HRID 2253574 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([O:13][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])[N:6]=1.Br[CH2:24][CH2:25][CH:26]1[O:30][CH2:29][CH2:28][O:27]1.Cl>C(Cl)(Cl)Cl.CN(C)C=O>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([O:4][CH3:3])[N:6]=[C:7]([O:13][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([O:18][CH2:24][CH2:25][CH:26]2[O:30][CH2:29][CH2:28][O:27]2)=[O:17])[N:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 1841852-((4,6-Dimethoxypyrimidin-2-yl)oxy)benzoic acid

Product 1

HCID 152782372-(1,3-Dioxolan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoateYield 63.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent3×

Procedure

10 Milliliters of N,N-dimethylformamide in which 0.22 g of 60% sodium hydride in oil has been suspended was mixed with 5 ml of N,N-dimethylformamide solution of 1.38 g of 2-(4,6-dimethoxypyrimidin-2-yl)oxy benzoic acid. After stirring the mixture at room temperature for 30 minutes, 10 ml of N,N-dimethylformamide solution of 1.81 g of 2-(2-bromoethyl)-1,3-dioxolane was added thereto. The resulting solution was stirred at 100° to 110° C. for 2 hours. The reaction solution was allowed to cool, poured into diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer separated from the aqueous layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue obtained was subjected to silica gel column chrmatography (mfd. by Merck & Co., Inc., solvent: chloroform) to obtain 1.20 g of 2-(1,3-dioxolan-2-yl)ethyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate [present compound (V-2)].

Workup

  1. stirringThe resulting solution was stirred at 100° to 110° C. for 2 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. customThe organic layer separated from the aqueous layer
  5. washwas washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue obtained

Sources & evidence

ORD record
ord-53f952c66be04e898d1456501b04b68a
Source dataset
uspto-grants-1993_08
Patent number
US05232897

Reaction notes

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