1,5-Bis(2-hydroxyphenyl)-1,4-pentadien-3-one → HCID 68698394, compound

HRID 2222256Notes

Reaction equation

HRID 2222256 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].[BH4-].[Na+]>C1COCC1.CO>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][CH:10]([OH:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19]

Participants

4

Reactant 2

HCID 981761,5-Bis(2-hydroxyphenyl)-1,4-pentadien-3-oneHCID 4311764Sodium borohydride

Product 1

HCID 68698394HCID 68698394, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 1,5-bis(2-hydroxyphenyl)penta-1,4-dien-3-one (EF1) (109 mg, 0.41 mmol) in THF/methanol (10/1) (2.5 mL) was added NaBH4 (40 mg, 1.30 mmol) in one portion at 0° C. After stirring for 30 min at this temperature the reaction was quenched with H2O dist and cold brine, diluted with Et2O (10 mL) and neutralized by bubbling CO2 through the dark-red solution (color change to pale yellow). The aqueous phase was extracted with ether, the combined ether layers washed with brine, dried over MgSO4 and concentrated. The crude product was purified by chromatography on silica gel using 30% EtOAc/hexanes. The product was obtained as a white solid (66%). 1H NMR (300 MHz, CDCl3) δ 7.27 (2H, dd, J=8.0 Hz, J=2.4 Hz), 7.21 (1H, s-br), 7.14-7.06 (3H, m), 6.90-6.83 (3H, m), 6.80-6.74 (2H, m), 6.18 (1H, dd, J=20.8 Hz, J=8.8 Hz), 5.99 (1H, s-br), 4.24 (1H, t-deformed), 3.23 (1H, s-br), 2.86 (1H, m), 2.71 (1H, m), 1.91 (2H, m). 13C NMR (75 MHz, CDCl3) δ 154.25, 152.96, 132.84, 130.75, 129.03, 127.79, 127.62, 127.46, 125.71, 123.97, 121.12, 121.07, 116.42, 116.22, 72.09, 37.57, 25.76.

Workup

  1. customwas quenched with H2O dist and cold brine
  2. additiondiluted with Et2O (10 mL)
  3. customby bubbling CO2 through the dark-red solution (color change to pale yellow)
  4. extractionThe aqueous phase was extracted with ether
  5. washthe combined ether layers washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel using 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-06204a85d0fd4afeaa52b60f9ee90982
Source dataset
uspto-grants-2008_05
Patent number
US07371766B2

Reaction notes

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