Ethyl chloroacetate → Ethyl-5-[(hydroxyimino)methyl]-2-nitro-3-thiopheneacetate

HRID 1860269

反応式

HRID 1860269 の反応式
CC(C)([O-])C.[K+].[N+:7]([C:10]1[S:14][C:13]([CH:15]=[N:16][OH:17])=[CH:12][CH:11]=1)([O-:9])=[O:8].Cl[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:11]1[CH:12]=[C:13]([CH:15]=[N:16][OH:17])[S:14][C:10]=1[N+:7]([O-:9])=[O:8])[CH3:24]

参加物

5

反応物 3

HCID 7751Ethyl chloroacetateHCID 3505165-Nitro-2-thiophenecarboxaldehyde oximeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 85801896Ethyl-5-[(hydroxyimino)methyl]-2-nitro-3-thiopheneacetate収率 27.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-30 °C

実験手順

Potassium tertiary-butoxide (960 mg, 8.6 mmol) was dissolved in N,N-dimethylformamide (10 ml) and the solution cooled to −30° C. A solution of 5-nitro-2-thiophenecarboxaldehyde oxime (400 mg, 2.86 mmol) and ethyl chloroacetate (356 mg, 2.86 mmol) was added dropwise in dry N,N-dimethylformamide (5 ml) over 5 minutes. The reaction mixture was stirred at −30° C. for 30 minutes then quenched with 2M HCl (50 ml), diluted with ethyl acetate, washed with water, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel using hexane/diethyl ether (1:2) as eluent to give 200 mg of ethyl-5-[(hydroxyimino)methyl]-2-nitro-3-thiopheneacetate as a tan solid. MS(ES): m/e 227 [M+H].

後処理

  1. customthen quenched with 2M HCl (50 ml)
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-3725d1bfa4d54d478308ee4da6cc06a7
出典データセット
uspto-grants-2003_03
特許番号
US06528653B2

関連ノート

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