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

HRID 1741414

反応式

HRID 1741414 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-ade7e75b1a8a4fae9720327ce81bd397
出典データセット
uspto-grants-1999_10
特許番号
US05972965

関連ノート

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