Dimethyl Sulfoxide → 2-(4-Fluoro-benzyl)-5-(2-nitro-ethyl)-furan

HRID 1694201Notes

Reaction equation

HRID 1694201 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2[O:8][C:9](/[CH:12]=[CH:13]/[N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.CS(C)=O.[BH4-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[O:8][C:9]([CH2:12][CH2:13][N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592553892-(4-Fluoro-benzyl)-5-((E)-2-nitro-vinyl)-furan

Product 1

HCID 592552022-(4-Fluoro-benzyl)-5-(2-nitro-ethyl)-furanYield 93.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(4-fluoro-benzyl)-5-((E)-2-nitro-vinyl)-furan (1.21 g, 4.89 mmol) described in Manufacturing Example 208-1-3 in acetic acid (0.6 mL) and dimethyl sulfoxide (10 mL) was added sodium borohydride (296 mg, 7.82 mmol), which was stirred for 30 minutes at room temperature. The mixture was cooled with ice water 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 (1.14 g). The title compound was used in the following reaction without any further purification.

Workup

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

Sources & evidence

ORD record
ord-554d043f77494e8d86f25ee4c4dba573
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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