Tetrahydrofuran → HCID 67024288, compound

HRID 384097Notes

Reaction equation

HRID 384097 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([OH:20])[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].[O:23]1[CH2:27]CC[CH2:24]1>C(N(CC)CC)C.COCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([O:20][CH2:24][O:23][CH3:27])[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178515651HCID 178515651, compound

Product 1

HCID 67024288HCID 67024288, compound

Reagents, catalysts & solvents 2

HCID 7864Chloromethyl Methyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 5-(4-(benzyloxy)phenyl)isoxazol-3-ol (1.38 g) in tetrahydrofuran (30 ml), 2.15 ml of triethylamine and 0.51 ml of methoxymethyl chloride were added, and the reaction solution was stirred overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (10:90-0:100)) to afford the title compound as a light brown solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (10:90-0:100))

Sources & evidence

ORD record
ord-5837cd8ae23f41ab95e191c9ef37f3f2
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

Loading…