Triethylamine → 1-[4,5-Bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione

HRID 1741414

반응식

HRID 1741414 반응식
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[O:8][C:9]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:11]=1)=[O:6].C(N(CC)CC)C.N1C=CC=CC=1S(O)(=O)=O>CS(C)=O>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:11]=[C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH:2]=[O:1])[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 948492-Pyridinesulfonic acidHCID 183673354-Hydroxy-1-(4,5-bis(4-methylphenyl)-oxazol-2-yl)butan-1-one

생성물 1

HCID 183673471-[4,5-Bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione수율 28.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a solution of 4-hydroxy-1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1-one (0.78 g) and triethylamine (2 ml) in DMSO (10 ml) was added a solution of pyridinesulfonic acid (1.16 g) in DMSO (4 ml) at room temperature. After being stirred for 20 minutes at the same temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1M-HCl, water and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione (0.22 g). MS (m/z): 334 (M+ +1) IR (Nujol): 1735, 1690 cm-1NMR (CDCl3, δ): 2.38 (3H, s), 2.40 (3H, s), 2.97 (2H, t, J=6.4 Hz), 3.47 (2H, t, J=6.4 Hz), 7.17-7.26 (4H, m), 7.53-7.59 (4H, m), 9.88 (1H, s)

후처리

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with 1M-HCl, water and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-ade7e75b1a8a4fae9720327ce81bd397
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05972965

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