Hydrochloric Acid → Tetrahydrofurfuryl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate

HRID 2253575Notes

Reaction equation

HRID 2253575 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])[N:4]=1.[CH2:21](O)[CH:22]1[O:26][CH2:25][CH2:24][CH2:23]1.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(Cl)(=O)=O)(C)C.CN1C=CN=C1.Cl>O1CCCC1.C(Cl)(Cl)Cl>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([O:16][CH2:21][CH:22]2[O:26][CH2:25][CH2:24][CH2:23]2)=[O:15])[N:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 13901-MethylimidazoleHCID 7360Tetrahydrofurfuryl alcoholHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 1841852-((4,6-Dimethoxypyrimidin-2-yl)oxy)benzoic acid

Product 1

HCID 15278238Tetrahydrofurfuryl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.55 Gram of 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid, 0.21 g of tetrahydrofurfuryl alcohol and 0.85 g of 2,4,6-triisopropylbenzenesulfonyl chloride were dissolved in 5 ml of tetrahydrofuran. Subsequently, 0.45 g of 1-methylimidazole was added to the mixture. After stirring the resulting solution at room temperature for 1 hour in order to carry out the reaction, the reaction solution was 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 chromatography (mfd. by Merck & Co., Inc., solvent: chloroform) to obtain 0.30 g of tetrahydrofurfuryl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate [present compound (III-g)].

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate
  3. customThe organic layer separated from the aqueous layer
  4. washwas washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue obtained

Sources & evidence

ORD record
ord-63c0a274bede438193bf4c2f67c535ad
Source dataset
uspto-grants-1993_08
Patent number
US05232897

Reaction notes

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