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Hydrochloric Acid → 3-{4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester

HRID 1993033
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HRID 1993033 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14].[CH2:25]([O:27][C:28](=[O:41])[CH2:29][CH:30]([C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)[C:31]#[C:32][CH3:33])[CH3:26].Cl>CN(C=O)C.O>[CH2:25]([O:27][C:28](=[O:41])[CH2:29][CH:30]([C:34]1[CH:35]=[CH:36][C:37]([O:40][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:38][CH:39]=1)[C:31]#[C:32][CH3:33])[CH3:26]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazoleHCID 59132733Ethyl 3-(4-hydroxyphenyl)hex-4-ynoate

생성물 1

HCID 591326383-{4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Cesium carbonate (0.51 g, 1.57 mmol) was added to a solution of 18.2 (216 mg, 0.79 mmol) and phenol 16 (220 mg, 0.79 mmol) in DMF (8 mL). The reaction was stirred at room temperature overnight and then taken up in water (500 mL). The solution was adjusted to pH=4.0 with 1N HCl(aq) and extracted with ethyl acetate (2×25 mL). The combined organics were washed with water, followed by brine. The solvent was removed under reduced pressure and the resulting residue was purified via radial chromatography (20% diethyl ether in hexanes) to yield 304 mg (82%) of 3-{4-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester. LC/MSD m/e: 472.0 (M+H); 1H NMR (400 MHz) (CDCl3) δ 8.16 (2H, d, J=8.0 Hz), 7.73 (2H, d, J=8.0 Hz), 7.33 (2H, m), 6.99 (2H, m), 5.01 (2H, s), 4.14 (3H, m), 2.72 (2H, m), 2.48 (3H, s), 1.85 (3H, s), 1.26 (3H, t, J=8.0 Hz).

후처리

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. washThe combined organics were washed with water
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting residue was purified via radial chromatography (20% diethyl ether in hexanes)

출처 및 근거

ORD 기록
ord-3422f5665d9e40caac72148b944f5149
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07649110B2

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