Sodium borohydride → 1504-63-8

HRID 351915Notes

Reaction equation

HRID 351915 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7](/[CH:8]=[CH:9]/[CH:10]=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7](/[CH:8]=[CH:9]/[CH2:10][OH:11])=[CH:12][CH:13]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53541354-Nitrocinnamaldehyde

Product 1

HCID 54628941504-63-8

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-4-Nitrocinnamaldehyde (3,1.0 g, 5.65 mmol) was dissolved in methanol (70 ml ) in a 100 ml flask. Sodium borohydride (106 mg, 2.8 mmol) was added portionwise while stirring. Stirring was continued for 0.5 hr. The solution was evaporated to dryness. The residue was dissolved in a chloroform/water mixture and the organic phase was separated. It was washed twice with distilled water and dried over anhydrous MgSO4. Evaporation of solvent and crystallization from CH2Cl2-hexanes yielded compound 4 (1.0 g, 98%) as a pale yellow solid: mp 129-130° C.; Rf=0.77 (10%CH3OH—CH2Cl2); 1H NMR (300 MHz, CDCl3): δ8.20 (d, aromatic, 2H, J=8.0 Hz), 7.53) (d, aromatic, 2H, J=8.0 Hz), 6.73) (d, 1H, J=16 Hz), 6.57 (m, 1H), 4.20 (d, 2H, J=5.2 Hz), 1.56 (s, 1H); 13C NMR (CDCl3): δ147.16(C), 143.48(C), 133.81(CH), 128.46(CH), 127.13(CH), 124.23(CH), 63.30(CH2).

Workup

  1. stirringStirring
  2. customThe solution was evaporated to dryness
  3. dissolutionThe residue was dissolved in a chloroform/water mixture
  4. customthe organic phase was separated
  5. washIt was washed twice with distilled water
  6. dry with materialdried over anhydrous MgSO4
  7. customEvaporation of solvent and crystallization from CH2Cl2-hexanes yielded compound 4 (1.0 g, 98%) as a pale yellow solid

Sources & evidence

ORD record
ord-2c6e2f39459747dd900c3cc14a020ebe
Source dataset
uspto-grants-2004_06
Patent number
US06743820B2

Reaction notes

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