Cesium carbonate → HCID 11025958、化合物

HRID 1609906ノート

反応式

HRID 1609906 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15]S(C1C=CC(C)=CC=1)(=O)=O.[CH2:26]([O:28][C:29](=[O:41])[C:30]([O:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=1)([CH3:32])[CH3:31])[CH3:27].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:26]([O:28][C:29](=[O:41])[C:30]([CH3:32])([O:33][C:34]1[CH:39]=[CH:38][C:37]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:36][CH:35]=1)[CH3:31])[CH3:27]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoateHCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonate

生成物 1

HCID 11025958HCID 11025958、化合物収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of the toluene-4-sulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester (See Japan Tobacco Inc International Application Wo 9518125) (24 g, 66.9 mmol), 2-(4-hydroxyphenoxy)-2-methylpropanoic acid ethyl ester (See American Home Products U.S. Pat. No. 3,795,691) (12.5 g, 55.71 mmol) and Cs2CO3 (22.7 g, 69.6 mmol) was heated at 55° C. in DMF (45 mL) for 18 h. The reaction was partitioned between EtOAc (160 mL) and H2O (180 mL), and the aqueous phase extracted with EtOAc (150 mL). The combined organic phases were dried (MgSO4) and concentrated under reduced pressure to an oil which was purified by column chromatography (1500 mL SiO2, 10% EtOAc/hexanes to 20% EtOAc/hexanes) to provide 2-methyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]-phenoxy}propionic acid ethyl ester (17.8 g, 78%) as a colorless, viscous oil: Rf=0.48 in 35% EtOAc/hexanes; 1H NMR (400 MHz, CDCl3) δ 7.99-7.96 (m, 2H), 7.43-7.40 (m, 3H), 6.83-6.75 (m, 4H), 4.22 (q, J=9.2 Hz, 2H), 4.18 (t, J=8.8 Hz, 2H), 2.95 (t, J=8.8 Hz, 2H), 2.36 (s, 3H), 1.52 (s, 6H), 1.27 (t, J=9.2 Hz, 3H).

後処理

  1. customThe reaction was partitioned between EtOAc (160 mL) and H2O (180 mL)
  2. extractionthe aqueous phase extracted with EtOAc (150 mL)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure to an oil which
  5. customwas purified by column chromatography (1500 mL SiO2, 10% EtOAc/hexanes to 20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-e825a54d14bb4e80b578a6956cb9ebeb
出典データセット
uspto-grants-2006_01
特許番号
US06982278B2

反応ノート

読み込み中…