1,5-Bis(2-hydroxyphenyl)-1,4-pentadien-3-one → HCID 136381055, compound

HRID 2222257Notes

Reaction equation

HRID 2222257 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[CH:13][C:14](=O)[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]>CO.C(Cl)(Cl)Cl>[CH3:3][O:2][N:4]=[C:14]([CH:13]=[CH:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[OH:5])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]

Participants

4

Reactant 2

HCID 981761,5-Bis(2-hydroxyphenyl)-1,4-pentadien-3-oneHCID 521874O-Methylhydroxylamine hydrochloride2×

Product 1

HCID 136381055HCID 136381055, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Methoxyl-amine hydrochloride (30-35 wt % in H2O, 0.30 mL, 1.12 mmol) was added in one portion to a solution of 1,5-bis(2-hydroxyphenyl)penta-1,4-dien-3-one (EF1) in methanol/CHCl3 (2/3) (5 mL). The reaction proceeded at room temperature for 24 hrs, then additional methoxylamine hydrochloride (0.15 mL, 0.56 mmol) was added and the reaction stirred for an additional 24 hrs. After completion (TLC) the solvent was evaporated, the residue dissolved in methanol, stirred with silica gel and purified after concentration by chromatography on silica gel using 30% EtOAc/hexanes. The product was obtained as a pale yellow foam (86%). 1H NMR (400 MHz, CDCl3) δ 7.56 (1H, dd, J=8.0 Hz, J=1.6 Hz), 7.48 (1H, dd, J=8.0 Hz, J=1.6 Hz), 7.41 (1H, d, J=16.0 Hz), 7.39 (1H, d, J=16.8 Hz), 7.28 (1H, d, J=16.8 Hz), 7.20-7.13 (2H, m), 6.97-6.90 (2H, m), 6.94 (1H, d, J=16.0 Hz), 6.80 (1H, dd, J=8.0 Hz, J=1.6 Hz), 5.53 (1H, s-br), 5.36 (1H, s-br), 4.02 (3H, s). 13C NMR (100 MHz, CDCl3) δ 155.43, 153.86, 153.70, 132.28, 130.25, 130.10, 129.71, 128.00, 127.91, 124.16, 123.88, 123.57, 121.40, 121.30, 118.45, 116.37, 116.33, 62.41.

Workup

  1. customAfter completion (TLC) the solvent was evaporated
  2. dissolutionthe residue dissolved in methanol
  3. stirringstirred with silica gel
  4. custompurified
  5. concentrationafter concentration by chromatography on silica gel using 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-e057b7cdda14444c8fd893afd9214e00
Source dataset
uspto-grants-2008_05
Patent number
US07371766B2

Reaction notes

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