Sodium ethoxide → HCID 57809844, compound

HRID 2106002Notes

Reaction equation

HRID 2106002 reaction equation
[CH3:1][C:2]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[OH:21][CH2:22][C:23]1[C:28]([CH3:29])=[C:27]([OH:30])[C:26]([CH3:31])=[CH:25][N:24]=1.[O-]CC.[Na+]>C(O)C.C(OCC)(=O)C>[O:19]1[C:20]2[C:12]([C:2]([CH3:1])([CH3:11])[CH2:3][C:4]([OH:5])([C:7]([F:9])([F:10])[F:8])[CH2:6][N:24]3[CH:25]=[C:26]([CH3:31])[C:27](=[O:30])[C:28]([CH3:29])=[C:23]3[CH2:22][OH:21])=[CH:13][CH:14]=[CH:15][C:16]=2[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 577755187-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuranHCID 178430566HCID 178430566, compound

Product 1

HCID 57809844HCID 57809844, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran (30.0 mg) and 2-hydroxymethyl-3,5-dimethylpyridin-4-ol (32.2 mg) in anhydrous ethanol (0.25 mL) was added sodium ethoxide (21 wt. % solution in ethanol, 39.0 μL). After heating at 85° C. for 18 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 4% to 7% methanol-methylene chloride) to give the title compound as a white solid (10.4 mg), m.p. 160° C.-162° C.

Workup

  1. dry with materialdried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography with silica gel (eluted with 4% to 7% methanol-methylene chloride)

Sources & evidence

ORD record
ord-0a67d670c91f4d98bd2b4d1b7ee7fd09
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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