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

HRID 2097255노트

반응식

HRID 2097255 반응식
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]

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 178473089HCID 178473089, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6b4507e0d7d64365b47427f46dadbca9
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450310B2

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