Diisopropylethylamine → 6-(2,5-Difluorophenyl)-3,4-dihydro-3-methylene-5-nitro-2H-pyran

HRID 2244571Notes

Reaction equation

C(N(CC)C(C)C)(C)C.[N+:10]([CH2:13][C:14]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[F:23])=[O:15])([O-:12])=[O:11].I[CH2:25][C:26]([CH2:28]I)=[CH2:27]>CN(C)C=O>[CH2:25]=[C:26]1[CH2:28][C:13]([N+:10]([O-:12])=[O:11])=[C:14]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[O:15][CH2:27]1

Participants

Conditions

Temperature: 60 °C

Procedure

N,N-diisopropylethylamine (184 mL) was added to a solution of 2-nitro-1-(2,5-difluorophenyl)ethanone (92.7 g, 461 mmol) in N,N-dimethylformamide (1000 mL) and 3-iodo-2-(iodomethyl)prop-1-ene (156 g, 507 mmol). The mixture was heated at 60° C. for 2 h, evaporated and purified by chromatography (silica gel, gradient 0-30% dichloromethane in hexane) to yield 3-methylene-5-nitro-6-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran.

Workup

customevaporated
custompurified by chromatography (silica gel, gradient 0-30% dichloromethane in hexane)

Sources & evidence

ORD record: ord-d7cfbd13f84743ddbcb552b56b5684ef
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678905B2

Reaction notes

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