Cesium carbonate → HCID 11025958, 화합물

HRID 1609906노트

반응식

HRID 1609906 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 11025958HCID 11025958, 화합물수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e825a54d14bb4e80b578a6956cb9ebeb
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982278B2

반응 노트

불러오는 중…