Sodium hydride → (2-Fluoro-4-methoxycarbonylmethoxy-5-nitrophenyl) 1-pyrrolidinecarboxylate

HRID 981864Notes

Reaction equation

[N:1]1([C:6]([O:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12](F)=[CH:11][C:10]=2[F:19])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]([O:24][CH3:25])(=[O:23])[CH2:21][OH:22].[H-].[Na+]>O1CCCC1>[N:1]1([C:6]([O:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]([O:22][CH2:21][C:20]([O:24][CH3:25])=[O:23])=[CH:11][C:10]=2[F:19])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: -50 °C

Procedure

To a stirred, cold (-50° ) mixture of 7.00 g (0.0257 mole) of (2,4-difluoro-5-nitrophenyl) 1-pyrrolidinecarboxylate and 1.60 g (0.0283 mole) of methyl glycolate in 200 mL of tetrahydrofuran was added 1.02 g (0.0424 mole) of sodium hydride. The reaction mixture was stirred at -50° C. for approximately four hours. The mixture was allowed to gradually warm to room temperature. The reaction mixture was poured into ice-water, and the resultant mixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to yield 4.5 g of (2-fluoro-4-methoxycarbonylmethoxy-5-nitrophenyl) 1-pyrrolidinecarboxylate. The nmr and ir spectra were consistent with the proposed structure.

Workup

temperatureto gradually warm to room temperature
extractionthe resultant mixture was extracted with diethyl ether
dry with materialThe extract was dried over anhydrous magnesium sulfate
filtrationfiltered
customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record: ord-6b03fd6c8368413498ba52be6f1600d9
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994104

Reaction notes

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