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Cesium carbonate → HCID 69869841, 화합물

HRID 2229025
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HRID 2229025 반응식
[CH2:1]([C:4]1[CH:5]=[C:6]([OH:31])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18])[CH2:2][CH3:3].Br[C:33]([CH3:40])([CH3:39])[C:34]([O:36][CH2:37][CH3:38])=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:37]([O:36][C:34](=[O:35])[C:33]([O:31][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:23][CH:24]=3)[O:16][C:17]=2[CH3:18])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:5]=1)([CH3:40])[CH3:39])[CH3:38]
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 22633446HCID 22633446, 화합물

생성물 1

HCID 69869841HCID 69869841, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

A mixture of 3-propyl-4-[2-(5-methyl-2-biphenyl-4-yl-oxazole-4-yl)ethoxy]phenol (0.90 mmol), ethyl 2-bromo-2-methylpropanoate (2.25 mmol) and cesium carbonate (0.45 g, 1.38 mmol) in anhydrous DMF (4 mL) was heated for 24 h at 55° C. The mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (40 mL), washed with brine, dried (Na2SO4), and removed in vacuo to give a crude oil which was purified using radial chromatography eluting with 2% ethyl acetate/Dichloromethane to give 2-{4-[2-(2-biphenyl-4-yl-5-methyloxazol-4-yl)ethoxy]-3-propylphenoxy}-2-methylpropionic acid ethyl ester, 1H NMR (400 MHz, CDCl3) δ8.04 (dd, J=8.3 Hz, 2H) 7.67 (d, J=3.4 Hz, 1H), 7.65 (dd, J=6.8, 2.0 Hz, 7.62 (d, J=2.9 Hz, 1H), 7.45 (t, J=6.6 Hz, 2H), 7.37 (t, J=7.8 Hz, 2H), 6.72-6.61 (m, 3H), 4.25 (q, J=7.1 Hz, 2H), 4.20 (t, J=6.6 Hz, 2H), 2.95 (t, J=7 Hz, 2H), 2.48, (t, J=7 Hz, 1H), 2.38 (s, 3H), 1.53-1.48 (m, 8H), 1.25 (t, J=7 Hz, 3H), 0.88 (t, J=7.1 Hz, 3H); MS (FIA) m/e 528 (M+1).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate (50 mL) and water (40 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customremoved in vacuo
  6. customto give a crude oil which
  7. customwas purified
  8. washeluting with 2% ethyl acetate/Dichloromethane

출처 및 근거

ORD 기록
ord-26bee7e1f8094b7fac4e8b9cbfbfed9d
출처 데이터셋
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06417212B1

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