Acetic Acid → HCID 57626338, compound

HRID 640252Notes

Reaction equation

HRID 640252 reaction equation
C(O)(=O)C.[CH2:5]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](/[CH:16]=[CH:17]/[N+:18]([O-:20])=[O:19])[CH:11]=1)[CH2:6][CH2:7][CH3:8].[BH4-].[Na+]>CS(C)=O>[CH2:5]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][N+:18]([O-:20])=[O:19])[CH:11]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 22158308HCID 22158308, compound

Product 1

HCID 57626338HCID 57626338, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an acetic acid (3.9 mL) and dimethyl sulfoxide (67 mL) solution of 1-butoxy-3-((E)-2-nitro-vinyl)-benzene (3.92 g, 17.7 mmol) described in Manufacturing Example 65-1-2 was added sodium borohydride (1.07 g, 28.3 mmol) at room temperature while cooling appropriately. This mixture was stirred for 4 hours at room temperature. This mixture was 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, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (2.29 g, 58%).

Workup

  1. temperaturewhile cooling appropriately
  2. customThis mixture was partitioned 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
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-c1217b977599485f964c9abe4db166d8
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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