Acetic Acid → 1-Cyclohexyloxy-4-(2-nitro-ethyl)-benzene

HRID 1691130Notes

Reaction equation

HRID 1691130 reaction equation
C(O)(=O)C.[CH:5]1([O:11][C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[N+:20]([O-:22])=[O:21])=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[BH4-].[Na+]>CS(C)=O>[CH:5]1([O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][N+:20]([O-:22])=[O:21])=[CH:16][CH:17]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 59255256HCID 59255256, compound

Product 1

HCID 592550821-Cyclohexyloxy-4-(2-nitro-ethyl)-benzeneYield 44.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an acetic acid (3.3 mL) and dimethyl sulfoxide (55 mL) solution of 1-cyclohexyloxy-4-((E)-2-nitro-vinyl)-benzene (3.3 g, 13.1 mmol) described in Manufacturing Example 79-1-2 was added sodium borohydride (793 mg, 21 mmol) at room temperature while cooling appropriately. This mixture was stirred for 1 hour 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=4:1) to obtain the title compound (1.45 g, 44%).

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=4:1)

Sources & evidence

ORD record
ord-3f385cb16cb349c3905006e6d8af9d88
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

Loading…