Nitromethane → 2-(4-Fluoro-benzyl)-5-((E)-2-nitro-vinyl)-furan

HRID 1691352Notes

Reaction equation

HRID 1691352 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2[O:11][C:10]([CH:12]=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[N+:16]([CH3:19])([O-:18])=[O:17].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2[O:11][C:10](/[CH:12]=[CH:19]/[N+:16]([O-:18])=[O:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 592551775-(4-Fluorobenzyl)furan-2-carbaldehyde

Product 1

HCID 592553892-(4-Fluoro-benzyl)-5-((E)-2-nitro-vinyl)-furanYield 100.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-fluoro-benzyl)-furan-2-carbaldehyde (1 g, 4.89 mmol) described in Manufacturing Example 208-1-2, nitromethane (1.32 mL, 24.5 mmol), ammonium acetate (754 mg, 9.78 mmol), and acetic acid (10 mL) was stirred for 3 hours at 100° C. This mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (1.21 g). The title compound was used in the following reaction without any further purification.

Workup

  1. temperatureThis mixture was cooled to room temperature
  2. custompartitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-592c700ded254e1ebbd06c31d8249f0b
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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