N-Iodosuccinimide → Ethyl 4-iodo-5-phenylisoxazole-3-carboxylate

HRID 1804447노트

반응식

HRID 1804447 반응식
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:17]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[I:17][C:8]1[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][O:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 571142Ethyl 5-phenylisoxazole-3-carboxylate

생성물 1

HCID 58537206Ethyl 4-iodo-5-phenylisoxazole-3-carboxylate수율 100%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A mixture of ethyl 5-phenylisoxazole-3-carboxylate (406 mg, 1.87 mmol) and N-iodosuccinimide (505 mg, 2.24 mmol) in trifluoroacetic acid (10 mL) was stirred at room temperature for 1.5 h. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with a 1N aqueous solution of sodium hydroxide (50 mL), washed with a 2.5% aqueous solution of sodium bisulfite (50 mL), washed with brine (50 mL), and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded ethyl 4-iodo-5-phenylisoxazole-3-carboxylate (641 mg, 1.87 mmol, 100% yield) as a light yellow oil. The compound had an HPLC retention time=3.36 minutes (YMC-Combi 4.6×50 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.2% phosphoric acid over a 4 minute gradient. MS: (M+H)=343.97. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (t, J=7.1 Hz, 3H), 4.50 (q, J=7.0 Hz, 2H), 7.52-7.56 (m, 3H), and 8.05 (m, 2H).

후처리

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide (50 mL)
  4. washwashed with a 2.5% aqueous solution of sodium bisulfite (50 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-9c449d374a38494bb620ab5528b28b7e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354398B2

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