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

HRID 1860269

Reaction equation

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]

Participants

Conditions

Temperature: -30 °C

Procedure

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].

Workup

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

Sources & evidence

ORD record: ord-3725d1bfa4d54d478308ee4da6cc06a7
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528653B2

Linked notes

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