Ethanol → Ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate

HRID 389926Notes

Reaction equation

HRID 389926 reaction equation
Cl.[NH2:2]O.[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([Cl:26])=[CH:14][C:13]=1[C:27](=[O:34])[CH:28]=[C:29](O)[C:30]([O-:32])=[O:31])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:35][CH2:36]O>>[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15]([Cl:26])=[CH:14][C:13]=1[C:27]1[O:34][N:2]=[C:29]([C:30]([O:32][CH2:35][CH3:36])=[O:31])[CH:28]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 178525988HCID 178525988, compound

Product 1

HCID 24774040Ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylateYield 80%

Procedure

Hydroxylamine hydrochloride (0.89 g, 12.8 mmol) was added to a suspension of 4-(2,4-bis(benzyloxy)-5-chlorophenyl)-2-hydroxy-4-oxobut-2-enoate (5.0 g, 10.7 mmol) in EtOH (100 ml). The reaction mixture was heated to reflux for 3.5 h and then allowed to cool to RT. The resulting suspension was filtered, washed sequentially with EtOH (2×10 ml), water (2×10 ml), and EtOH (2×10 ml), and dried under vacuo to afford the title compound ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate (3.97 g, 80%) as a flocculent light-yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 h
  3. filtrationThe resulting suspension was filtered
  4. washwashed sequentially with EtOH (2×10 ml), water (2×10 ml), and EtOH (2×10 ml)
  5. customdried under vacuo

Sources & evidence

ORD record
ord-dc8b0fd2a8394efc9d8ae15cb3f2ce42
Source dataset
uspto-grants-2013_02
Patent number
US08383616B2

Reaction notes

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