7-Hydroxyflavanone → 7-[2-(1H-1-Imidazolyl)ethoxy]-2-phenyl-4-chromanone

HRID 1859822Notes

Reaction equation

HRID 1859822 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[CH2:7][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:38]1([CH2:43][CH2:44]O)[CH:42]=[CH:41][N:40]=[CH:39]1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N:38]1([CH2:43][CH2:44][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:18])[CH2:7][CH:8]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[O:9]3)=[CH:4][CH:3]=2)[CH:42]=[CH:41][N:40]=[CH:39]1

Participants

6

Reactant 4

HCID 18907-HydroxyflavanoneHCID 11776TriphenylphosphineHCID 74168N-(2-Hydroxyethyl)imidazoleHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 154869117-[2-(1H-1-Imidazolyl)ethoxy]-2-phenyl-4-chromanoneYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.0 g (20.8 mmol) of 7-hydroxy-2-phenyl-4-chromanone in 200 mL of THF was treated with 6.22 g (23.7 mmol) of triphenylphosphine and 2.65 g (23.7 mmol) of 2-(1H-1-imidazolyl)-1-ethanol. A solution of 4.13 g (23.7 mmol) of diethyl azodicarboxylate in 25 mL of THF was added dropwise and the solution allowed to stir at room temperature overnight. The solvent was removed under pressure, and the residue taken up in 1N citric acid and washed three times with Et2O. The aqueous phase was adjusted to pH 7 with 50% NaOH and extracted with EtOAc. The EtOAc was washed with saturated NaCl and dried over MgSO4. Treatment with charcoal and removal of the solvent under pressure gave 3.0 g (43% yield) of the product as a white solid, mp 139-140° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 335 (M+H+).

Workup

  1. customThe solvent was removed under pressure
  2. washwashed three times with Et2O
  3. extractionextracted with EtOAc
  4. washThe EtOAc was washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. customTreatment with charcoal and removal of the solvent under pressure

Sources & evidence

ORD record
ord-a7d6c6d96a9647df966a2bab970bac1e
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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