Water → 2-(2,6-Difluorophenyl)-4,5-dihydro-4-[4-(2-naphthalenylmethoxy)-phenyl]oxazole

HRID 964319Notes

Reaction equation

HRID 964319 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[N:13]=1.Br[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 190801304-[2-(2,6-Difluorophenyl)-4,5-dihydro-1,3-oxazol-4-yl]phenol

Product 1

HCID 190801232-(2,6-Difluorophenyl)-4,5-dihydro-4-[4-(2-naphthalenylmethoxy)-phenyl]oxazoleYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 6 (0.36 g, 1.3 mmol) and 2-bromomethyl naphthalene (0.4 g, 1.7 mmol) were stirred at 23° C. for 18 h with potassium carbonate (0.6 g, 4 mmol) in dimethylformamide (10 mL). The mixture was poured into water (50 mL) and extracted with diethylether (50 mL). The diethylether was washed with water (50 mL) twice, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was subjected to silica gel chromatography using hexanes/ethyl acetate (6:1) as eluent to give the title compound as a solid (0.27 g): m.p. 148°-150° C. 1H NMR (CDCl3, 200 MHz) δ 7.8-7.0 (m,14H), 5.4 (m,1H), 5.2 (m,2H), 4.8 (m,1H), 4.3 (m,1H).

Workup

  1. extractionextracted with diethylether (50 mL)
  2. washThe diethylether was washed with water (50 mL) twice
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5136cca37c8f48dc8da060e9d9199209
Source dataset
uspto-grants-1998_06
Patent number
US05767281

Reaction notes

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