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

HRID 1294280
ノート
印刷プレビュー

反応式

HRID 1294280 の反応式
Cl[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:12][CH:13]=2)=[CH:5][CH:4]=1.[OH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][C:30]([O:32]C)=[O:31].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:14]1([C:11]2[S:12][CH:13]=[C:9]([CH2:8][O:7][C:6]3[CH:20]=[CH:21][C:3]([CH2:2][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:29][C:30]([OH:32])=[O:31])=[CH:4][CH:5]=3)[N:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 178613834-(4-Chloromethylphenoxy)methyl-2-phenylthiazole

生成物 1

HCID 688845582-[2-[4-[(2-Phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid収率 29.3%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A mixture of 4-(4-chloromethylphenoxymethyl)-2-phenylthiazole (1.95 g), methyl 2-(2-hydroxyphenyl)acetate (1.00 g), anhydrous potassium carbonate (0.85 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 (0.76 g, 29%) of 2-[2-[4-[(2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° 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-b9e5aa6b35f34ee5b149d48515a5773c
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07238716B2

反応ノート

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