Tetrahydrofuran → Methyl 3-(5-(benzyloxy)-2-methylphenyl)-5-(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 1486847Notes

Reaction equation

HRID 1486847 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:26])=[C:20]([C:22](Cl)=[N:23][OH:24])[CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:27]=[C:28]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:29]([O:31][CH3:32])=[O:30].C1COCC1>O>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:26])=[C:20]([C:22]2[CH2:27][C:28]([CH2:33][C:34]([O:36][CH3:37])=[O:35])([C:29]([O:31][CH3:32])=[O:30])[O:24][N:23]=2)[CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 69240Dimethyl itaconateHCID 1317368235-(Benzyloxy)-N-hydroxy-2-methylbenzenecarboximidoyl chloride

Product 1

HCID 118292791Methyl 3-(5-(benzyloxy)-2-methylphenyl)-5-(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (3.06 mL) was added to a mixture of 5-(benzyloxy)-N-hydroxy-2-methylbenzenecarboximidoyl chloride (6.05 g), dimethyl 2-methylenesuccinate (3.09 mL), and THF (100 mL) at room temperature, and the obtained mixture was stirred at 70 C for 2 hours. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The extract 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 (6.80 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract 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-8ec1980cd08c46c28dcaae3fa09c046a
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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