Sodium borohydride → HCID 28945889, compound

HRID 2266989Notes

Reaction equation

HRID 2266989 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[OH:2][CH2:1][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 132385393-(4-Formylphenoxy)benzonitrile

Product 1

HCID 28945889HCID 28945889, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(4-formyl-phenoxy)-benzonitrile of Preparation 10 (0.90 g, 4.04 mmol) in methanol (15 mL) and cool to 0° C. Add sodium borohydride (0.31 g, 8.08 mmol) in three batches. After 1 hr, allow to warm to ambient temperature and stir overnight. Concentrate under reduced pressure to give a residue. Dilute with ethyl acetate (50 mL) and wash with 1N hydrochloric acid (3×100 mL). Separate layers and dry the organic layer over magnesium sulfate, filter, and concentrate to a residue. Purification by flash chromatography, using 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes as a gradient eluent gives the title product (0.83 g, 91%): 1H NMR δ (CDCl3) 7.48-7.38 (m, 4H), 7.30-7.23 (m, 2H), 7.06 (d, J=8.4 Hz, 2H), 4.75 (s, 2H).

Workup

  1. dissolutionDissolve
  2. temperatureto warm to ambient temperature
  3. concentrationConcentrate under reduced pressure
  4. customto give a residue
  5. washwash with 1N hydrochloric acid (3×100 mL)
  6. dry with materialSeparate layers and dry the organic layer over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate to a residue
  9. customPurification by flash chromatography

Sources & evidence

ORD record
ord-7157fa46f22545d1a9b8fbec3916ae51
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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