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

HRID 488065

Reaction equation

HRID 488065 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.[O:21]1[CH2:25][CH2:24][CH2:23][CH:22]1O.[CH:27](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.C(OCC)(=O)C>[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][CH2:27][CH:22]2[O:21][CH2:25][CH2:24][CH2:23]2)=[O:15])[N:6]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 13901-MethylimidazoleHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 93002Tetrahydro-2-hydroxyfuranHCID 1841852-((4,6-Dimethoxypyrimidin-2-yl)oxy)benzoic acid

Product 1

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

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.55 Gram of 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoic acid, 0.21 g of tetrahydrofuryl 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 exracted 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 Merch & Co., Inc., solvent: chloroform) to obtain 0.30 g of tetrahydrofurfuryl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate [present compound (III-9)].

Workup

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

Sources & evidence

ORD record
ord-c5e8126c74af475bbb87348101a348c0
Source dataset
uspto-grants-1994_03
Patent number
US05298632

Linked notes

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