Hydrochloric Acid → (E)-Methyl 2-(2-chloro-6-nitrophenyl)-3-hydroxybut-2-enoate

HRID 453852

Reaction equation

[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].F[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].Cl>CN(C=O)C.O>[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:19]([O-:21])=[O:20])[C:12]=1/[C:2](=[C:3](\[OH:4])/[CH3:5])/[C:1]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 25 °C

Procedure

Methyl acetoacetate (59.82 mmol, 2.1 equiv.) was added dropwise at 0° C. to a suspension of NaH (65.52 mmol, 2.3 equiv.) in DMF (40 ml). Then the mixture was stirred for 10 min and subsequently heated to 25° C. 2-Fluoro-3-chloronitrobenzene (28.49 mmol, 1.0 equiv.) was cooled with an ice bath in a reaction flask, and the NaH suspension was added. Then stirring was carried out for 16 h at 25° C. 2 M HCl (5 ml) and water (10 ml) were then added, and extraction with diethyl ether (3×20 ml) was carried out. The combined organic phases were washed with water (10 ml) and sat. NaCl solution (20 ml), dried over Na2SO4 and reduced under reduced pressure. The residue was purified by column chromatography (5% ethyl acetate in hexane). Yield: 51%

Workup

stirringThen stirring
waitwas carried out for 16 h at 25° C
extractionextraction with diethyl ether (3×20 ml)
washThe combined organic phases were washed with water (10 ml) and sat. NaCl solution (20 ml)
dry with materialdried over Na2SO4
customThe residue was purified by column chromatography (5% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-2a72ef7018a54390acd9e8b8c1c119fb
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Linked notes

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