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Hydrochloric Acid → HCID 10992528、化合物

HRID 584410
ノート
印刷プレビュー

反応式

HRID 584410 の反応式
[H-].[Na+].[OH:3]/[N:4]=[C:5](\[CH3:11])/[C:6]([O:8]CC)=[O:7].Cl[CH2:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:16][CH:15]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:21][C:20]=1[CH2:19][O:18][C:17]1[CH:32]=[CH:33][C:14]([CH2:13][O:3]/[N:4]=[C:5](\[CH3:11])/[C:6]([OH:8])=[O:7])=[CH:15][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 9614318Ethyl 2-hydroxyiminopropionateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

生成物 1

HCID 10992528HCID 10992528、化合物収率 70%

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in oil, 127 mg) was added under a nitrogen atmosphere to a solution of ethyl E-2-hydroxyiminopropionate (418 mg) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.00 g) in N,N-dimethylformamide (10 ml) at room temperature and the mixture was stirred for 1 hour. After adding 1N HCl (5 ml), aqueous sodium bicarbonate was added, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residue was subjected to column chromatography on silica gel to obtain an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v). This oil was dissolved in tetrahydrofuran (10 ml)-methanol (5 ml), and 1N aqueous solution of sodium hydroxide (5 ml) was added and the mixture was stirred at room temperature for 1 hour. 1N HCl (5.5 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residual crystal was recrystallized from ethyl acetate-isopropylether to obtain E-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]propionic acid (849 mg, yield 70%) as colorless crystals. m.p. 147-148° C.

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto obtain an oil from a fraction
  7. washeluted with ethyl acetate-hexane (1:3
  8. dissolutionThis oil was dissolved in tetrahydrofuran (10 ml)-methanol (5 ml), and 1N aqueous solution of sodium hydroxide (5 ml)
  9. additionwas added
  10. stirringthe mixture was stirred at room temperature for 1 hour
  11. addition1N HCl (5.5 ml) was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated
  16. customThe residual crystal was recrystallized from ethyl acetate-isopropylether

出典と根拠

ORDレコード
ord-1405641a9b0640f787c433b5b4fc018a
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06924300B2

反応ノート

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