Thionyl Chloride → 4,5-Dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazole

HRID 251437Notes

Reaction equation

HRID 251437 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]1[CH:26]=[CH:25][C:16]([C:17]([NH:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=O)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[CH2:5]([O:12][C:13]1[CH:26]=[CH:25][C:16]([C:17]2[O:22][CH2:21][C:20]([CH3:24])([CH3:23])[N:19]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 141804474-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide

Product 1

HCID 149891694,5-Dihydro-4,4-dimethyl-2-[4-(phenylmethoxy)phenyl]oxazoleYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (11 ml, 150 mmol, 3 eq) is added to a solution of 4-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide ax1 (14.98 g, 50 mmol, 1 eq) in chloroform (400 ml) and the mixture is heated at reflux for 2 h. The solvent is then removed under vacuum, and the residue is dissolved into dichloromethane. The organic layer is washed with a saturated solution of aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under vacuum to give 2-[4-(benzyloxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole ax4 (4.3 g).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 h
  3. customThe solvent is then removed under vacuum
  4. dissolutionthe residue is dissolved into dichloromethane
  5. washThe organic layer is washed with a saturated solution of aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3de7717f549741829a55aa7d60e086fc
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

Loading…