Sodium Hypochlorite → tert-Butyl 3-(3-(benzyloxy)-5-bromophenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 1486886Notes

Reaction equation

HRID 1486886 reaction equation
Cl[O-].[Na+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14](/[CH:19]=[N:20]/[OH:21])[CH:15]=[C:16]([Br:18])[CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:22]=[C:23]([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C1COCC1.C(OCC)(=O)C.O>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([C:19]2[CH2:22][C:23]([CH2:31][C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[O:21][N:20]=2)[CH:15]=[C:16]([Br:18])[CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 23665760Sodium HypochloriteHCID 54559210Di-tert-butyl 2-methylidenebutanedioateHCID 118292821(NE)-N-[(3-bromo-5-phenylmethoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 118292799tert-Butyl 3-(3-(benzyloxy)-5-bromophenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylateYield 63.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

An aqueous sodium hypochlorite solution (5%, 7.92 g) was added dropwise to a solution of (E)-1-(3-(benzyloxy)-5-bromophenyl)-N-hydroxymethanimine (1.48 g) and di-tert-butyl 2-methylenesuccinate (1.171 g) in THF (15 mL) 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 (1.67 g).

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-81e4e1efde2a494d87455267bfc7e646
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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