Hydrochloric Acid → 2-[2-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid

HRID 1294281ノート

反応式

HRID 1294281 の反応式
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([O:33]C)=[O:32].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:14][C:13]1[S:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10][C:9]=1[CH2:8][O:7][C:6]1[CH:21]=[CH:22][C:3]([CH2:2][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][C:31]([OH:33])=[O:32])=[CH:4][CH:5]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 178613534-(4-Chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole

生成物 1

HCID 688842202-[2-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid収率 44.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole (2.13 g), methyl 2-(2-hydroxyphenyl)acetate (1.00 g), anhydrous potassium carbonate (1.65 g) and N,N-dimethylformamide (15 mL) was stirred overnight at room temperature. The reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. To a mixture of the obtained residue, tetrahydrofuran (10 mL) and methanol (10 mL) was added a 1N aqueous sodium hydroxide solution (10 mL) and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated, and dilute hydrochloric acid was added to the residue. The precipitated solid was collected by filtration and dried with air to give crystals (1.19 g, 44%) of 2-[2-[4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 122-123° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionTo a mixture of the obtained residue, tetrahydrofuran (10 mL) and methanol (10 mL)
  6. additionwas added a 1N aqueous sodium hydroxide solution (10 mL)
  7. stirringthe mixture was stirred at room temperature for 2 hrs
  8. concentrationThe reaction mixture was concentrated
  9. additiondilute hydrochloric acid was added to the residue
  10. filtrationThe precipitated solid was collected by filtration
  11. customdried with air

出典と根拠

ORDレコード
ord-efaeae9f0ab84006979d1167e80a5a8b
出典データセット
uspto-grants-2007_07
特許番号
US07238716B2

反応ノート

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