Sodium borohydride → HCID 68559635, compound

HRID 20442Notes

Reaction equation

HRID 20442 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[C:15](/[CH:17]=[CH:18]/[N+:19]([O-:21])=[O:20])[CH:14]=[C:13]([F:22])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl.C(O)(C)C>[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([CH2:17][CH2:18][N+:19]([O-:21])=[O:20])[CH:14]=[C:13]([F:22])[CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 685603091-benzyloxy-3-fluoro-5-((E)-2-nitro-vinyl)-benzene

Product 1

HCID 68559635HCID 68559635, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

Add sodium borohydride (1.69 g, 44.64 mmol) to 1-benzyloxy-3-fluoro-5-((E)-2-nitro-vinyl)-benzene (3.05 g, 11.16 mmol) and silica gel (22 g) in chloroform (112 mL) and isopropanol (33 mL) at room temperature in portions over 5 minutes. Stir at room temperature 90 minutes and filter. Concentrate and dissolve in ethyl acetate. Wash (10% potassium carbonate and saturated aqueous sodium chloride), dry over magnesium sulfate, filter and concentrate. Purify on 120 g silica gel eluting with 100:0 to 80:20 hexanes:ethyl acetate to afford 1.33 g (43.3%) of the desired compound as an oil.

Workup

  1. filtrationfilter
  2. concentrationConcentrate
  3. dissolutiondissolve in ethyl acetate
  4. washWash (10% potassium carbonate and saturated aqueous sodium chloride)
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify on 120 g silica gel eluting with 100:0 to 80:20 hexanes

Sources & evidence

ORD record
ord-024a788f0dd14e9895ec8a5bca3bfa73
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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