HCID 10353361, compound → HCID 57424364, compound

HRID 604332Notes

Reaction equation

HRID 604332 reaction equation
[N+:1]([CH2:4][C:5]([C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])=[O:6])([O-:3])=[O:2].I[CH2:17][C:18]([CH2:20]I)=[CH2:19]>CN(C)C=O.C(N(CC)C(C)C)(C)C>[CH2:17]=[C:18]1[CH2:20][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:7]2[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=2[F:15])[O:6][CH2:19]1

Participants

5

Reactant 2

HCID 10353361HCID 10353361, compoundHCID 110450293-Iodo-2-(iodomethyl)prop-1-ene

Product 1

HCID 57424364HCID 57424364, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-chloro-2-(chloromethyl)prop-1-ene (1.0 g, 8 mmol) and sodium iodide (6.6 g, 44 mmol) in acetone (60 mL) was stirred at room temperature for 20 hours, evaporated under reduced pressure and dissolved in dichloromethane (150 mL) and water (50 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to yield 3-iodo-2-(iodomethyl)prop-1-ene as a reddish oil (2.45 g). To a solution of 2-nitro-1-(2,4,5-trifluorophenyl)ethanone (110 mg, 0.5 mmol) in N,N-dimethylformamide (3 mL), N,N-diisopropylethylamine (0.20 mL) and 3-iodo-2-(iodomethyl)prop-1-ene (170 mg, 0.55 mmol) were added and the mixture was heated at 60° C. for 2.5 hours, evaporated and purified by chromatography on a Biotage Horizon® system (silica, gradient 0-30% dichloromethane in hexane) to yield 3-methylene-5-nitro-6-(2,4,5-trifluorophenyl)-3,4-dihydro-2H-pyran.

Workup

  1. customevaporated
  2. custompurified by chromatography on a Biotage Horizon® system (silica, gradient 0-30% dichloromethane in hexane)

Sources & evidence

ORD record
ord-8dc7f0a1e8ad45eca098d5d7b763e2ef
Source dataset
uspto-grants-2011_03
Patent number
US07910596B2

Reaction notes

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