Sodium borohydride → HCID 68790209, compound

HRID 2217608Notes

Reaction equation

HRID 2217608 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:29][OH:30])=[CH:27][CH:28]=2)=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 731978473-(3,5-Dimethoxyphenyl)-2-[4-(4-formylphenoxy)-phenyl]-acrylic acid methyl ester

Product 1

HCID 68790209HCID 68790209, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 9 (5.0 g, 11.9 mmol) was suspended in anhydrous ethanol (60 mL) at room temperature and sodium borohydride (0.23 g, 6.1 mmol) was added with efficient stirring. Reaction was complete in 1 h, solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was extracted with water (50 mL), brine (25 mL), dried on anhydrous magnesium sulfate, filtered and solvent was evaporated to yield the title compound 12 as white solid (5.1 g, 100%): mp 93-95° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.72 (s, 1H), 7.35 (d, J=8.8 Hz, 2H), 7.19 (d, J=8.8 Hz, 2H), 7.02 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.4 Hz, 2H), 6.41 (t, J=2.4 Hz, 1H), 6.29 (d, J=2.0 Hz, 2H), 5.18 (t, J=6.4 Hz, 1H), 4.49 (d, J=4.8 Hz, 2H), 3.73 (s, 3H), 3.57 (s, 6H); MS (EI) m/z 315[M]+. Anal. (C25H24O6) C, H.

Workup

  1. customReaction
  2. customsolvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. extractionThe organic layer was extracted with water (50 mL), brine (25 mL)
  5. dry with materialdried on anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customsolvent was evaporated

Sources & evidence

ORD record
ord-07774aacd4c540e4a871d8a3ab2db6ce
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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