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

HRID 646469ノート

反応式

HRID 646469 の反応式
Cl.[NH2:2]O.[CH2:4]([O:6][C:7](=[O:36])[C:8](O)=[CH:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:14][C:13]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:11])[CH3:5]>C(O)C>[CH2:4]([O:6][C:7]([C:8]1[CH:9]=[C:10]([C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:14][C:13]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:11][N:2]=1)=[O:36])[CH3:5]

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 178473089HCID 178473089、化合物

生成物 1

HCID 24774040Ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Hydroxylamine hydrochloride (0.89 g; 12.8 mmol) was added to a suspension of 4-(2,4-bis-benzyloxy-5-chlorophenyl)-2-hydroxy-4-oxo-but-2-enoic acid ethyl ester (5.00 g; 10.7 mmol) in absolute ethanol (100 ml). The reaction mixture was heated at reflux for four hours then allowed to cool to ambient temperature (during this time the mixture remains heterogeneous but becomes lighter yellow in colour). The mixture was filtered and the filtered solid was washed with water (2×20 ml), ethanol (2×20 ml) and dried in vacuo at 45° C. This affords 5-(2,4-bis-benzyloxy-5-chlorophenyl)-isoxazole-3-carboxylic acid ethyl ester as a fluffy yellow solid, 4.49 g (91%) LCMS: [M+H]+ 466, 464 (37Cl; 35Cl)). 1H NMR (400 MHz, CDCl3) δ 1.42 (t, 3H), 4.42 (q, 2H), 5.13 (s, 2H), 5.14 (s, 2H), 6.62 (s, 1H), 7.01 (s, 1H), 7.35-7.43 (m, 10H), 8.00 (s, 1H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for four hours
  3. filtrationThe mixture was filtered
  4. washthe filtered solid was washed with water (2×20 ml), ethanol (2×20 ml)
  5. customdried in vacuo at 45° C

出典と根拠

ORDレコード
ord-c2c17339400946579bb31295f249f1af
出典データセット
uspto-grants-2010_04
特許番号
US07705027B2

反応ノート

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