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

HRID 1860269

반응식

HRID 1860269 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
-30 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-3725d1bfa4d54d478308ee4da6cc06a7
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528653B2

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