Triphenylphosphine → 3-[1-(2-Chloro-phenyl)-ethoxy]-5-imidazol-1-yl-thiophene-2-carboxylic acid methyl ester

HRID 1171163노트

반응식

HRID 1171163 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([OH:29])[CH3:28].[CH3:30][O:31][C:32]([C:34]1[S:35][C:36]([N:40]2[CH:44]=[CH:43][N:42]=[CH:41]2)=[CH:37][C:38]=1O)=[O:33].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:30][O:31][C:32]([C:34]1[S:35][C:36]([N:40]2[CH:44]=[CH:43][N:42]=[CH:41]2)=[CH:37][C:38]=1[O:29][CH:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[Cl:20])[CH3:28])=[O:33]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 260821-(2-Chlorophenyl)ethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 546956113-Hydroxy-5-imidazol-1-yl-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 595539583-[1-(2-Chloro-phenyl)-ethoxy]-5-imidazol-1-yl-thiophene-2-carboxylic acid methyl ester수율 89.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Triphenyl phosphine (304 mg, 1.16 mmol, 1.3 Eq.), 1-(2-Chloro-phenyl)-ethanol (182 mg, 1.16 mmol, 1.3 Eq.) and 3-Hydroxy-5-imidazol-1-yl-thiophene-2-carboxylic acid methyl ester (200 mg, 0.89 mmol, 1.0 Eq.) in anhydrous THF (5 mL) were cooled to 0° C. under nitrogen. Diethyl azodicarboxylate (183 μL, 1.16 mmol, 1.3 Eq.) was added dropwise. The reaction was stirred at 0° C. for 30 minutes then warmed to ambient temperature for 3.5 hours. The solvent was removed in vacuo and the residue re-dissolved in DCM and absorbed onto SiO2. The crude product wad purifird by column chromatography (75% EtOAc/petroleum ether) to give the sub-title compound as a light yellow foam (290 mg, 0.80 mmol, 84%); 1H NMR (400 MHz, d-6 DMSO) δ 1.60 (3H, d), 3.80 (3H, s), 5.90 (1H, q), 7.14 (1H, d), 7.31-7.37 (1H, m), 7.43-7.49 (3H, m), 7.74-7.78 (2H, m), 8.29 (1H, d).

후처리

  1. temperaturethen warmed to ambient temperature for 3.5 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue re-dissolved in DCM
  4. customabsorbed onto SiO2

출처 및 근거

ORD 기록
ord-caf23616bdac4c4aa7c4045859846ddf
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829590B2

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