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Water → HCID 69472040, 화합물

HRID 854562
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HRID 854562 반응식
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:25]([O:27][C:28](=[O:41])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][C:32]=1[CH2:38][CH2:39][CH3:40])C.O>C(#N)C>[CH3:25][O:27][C:28](=[O:41])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:2][C:3]2[O:7][C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)=[N:5][C:4]=2[CH3:18])=[CH:33][C:32]=1[CH2:38][CH2:39][CH3:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 21300976HCID 21300976, 화합물HCID 57431964HCID 57431964, 화합물

생성물 1

HCID 69472040HCID 69472040, 화합물수율 85%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a suspension of 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (0.10 g, 0.36 mmol) and Cs2CO3 (0.24 g, 0.72 mmol) in 2 mL acetonitrile is added (4-hydroxy-2-propyl-phenoxy)-acetic acid ethyl ester (0.09 g, 0.38 mmol). The solution is stirred for 6 hrs and poured into water (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organics are washed with water (10 mL) and brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude product is purified using flash column chromatography (20% ethyl acetate/hexanes) to afford 0.13 g (85%) desired {4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-ylmethoxy]-2-propyl-phenoxy}-acetic acid methyl ester. This ester is hydrolyzed in the usual way using 0.14 g ester and 3 eq. 1M LiOH in 3 mL 3:2:1 THF:MeOH:H2O to afford 0.16 g (95%) of the title compound.

후처리

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe combined organics are washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified

출처 및 근거

ORD 기록
ord-47d42206af4a425cafc125d3b1a796dc
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07259175B2

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