Tetrahydrofuran → tert-Butyl 3-(3-(benzyloxy)-5-methylphenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 1486881Notes

Reaction equation

HRID 1486881 reaction equation
Cl[O-].[Na+].C1COCC1.[CH2:9]([O:16][C:17]1[CH:18]=[C:19](/[CH:24]=[N:25]/[OH:26])[CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:27]=[C:28]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C(OCC)(=O)C.O>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([C:24]2[CH2:27][C:28]([CH2:36][C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[O:26][N:25]=2)[CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 23665760Sodium HypochloriteHCID 54559210Di-tert-butyl 2-methylidenebutanedioateHCID 118292759(NE)-N-[(3-methyl-5-phenylmethoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 118292885tert-Butyl 3-(3-(benzyloxy)-5-methylphenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylateYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

An aqueous sodium hypochlorite solution (5%, 2715 mg) was added dropwise to a THF (4 mL) solution of (E)-1-(3-(benzyloxy)-5-methylphenyl)-N-hydroxymethanimine (400 mg) and di-tert-butyl 2-methylenesuccinate (402 mg) at 0 C, and the obtained mixture was stirred at 0 C for 2 hours and subsequently at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and water was added thereto. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (674 mg).

Workup

  1. additionwas added
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b725bb000d3e4fc4b468f02daeaa2924
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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