Triethylamine → Methyl [(4-phenyl)-5-(3,4-dichlorophenyl)oxazole] 2-butanoate

HRID 353485

반응식

HRID 353485 반응식
C[O:2][C:3]([CH2:5][CH2:6][CH2:7]CC(Cl)=O)=[O:4].[CH2:12]([N:14](CC)CC)[CH3:13].[Cl:19][C:20]1[CH:21]=[C:22]([CH:27]([OH:36])[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=O)[CH:23]=[CH:24][C:25]=1[Cl:26].C([O-])(=O)C.[NH4+]>C(Cl)Cl.C(O)(=O)C>[CH3:13][C:12]1[O:36][C:27]([C:22]2[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=2)=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:14]=1.[CH3:7][CH2:6][CH2:5][C:3]([OH:4])=[O:2]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 520737Methyl 6-chloro-6-oxohexanoateHCID 225052602-(3,4-Dichlorophenyl)-2-hydroxy-1(phenyl)ethanone

생성물 1

HCID 131723428Methyl [(4-phenyl)-5-(3,4-dichlorophenyl)oxazole] 2-butanoate수율 42,287.199%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회

실험 절차

5-(Methoxycarbonyl)pentanoyl chloride (2.82 g, 0.017 mol) and triethylamine (3.47 g, 0.034 mol) were added to a solution of 2-(3,4-dichlorophenyl)-2-hydroxy-1-[phenyl]ethanone (Step 1) (4.77 g, 0.017 mmol) in 40 mL of methylene chloride. The resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with 100 mL of methylene chloride. The organic solution was washed with water (1×100 mL), saturated brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was dried under high vacuum, then ammonium acetate (4.6 g, 0.06 mol) and 30 mL of acetic acid were added. The reaction mixture was heated at 100° C. for 2.5 h. The reaction mixture was cooled to room temperature, and the excess acetic acid was removed under vacuum. The resulting residue was partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was separated, washed with saturated aqueous sodium bicarbonate (2×100 mL), saturated brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was purified by flash chromatography on silica gel (eluting with 1:9 ethyl acetate:hexane) to give 2.82 g (42.6%) of methyl [(4-phenyl)-5-(3,4-dichlorophenyl)oxazole]-2-butanoate as a yellow oil: HRMS calcd. for C20H17N1O3Cl2 390.0664. Found 390.0648.

후처리

  1. washThe organic solution was washed with water (1×100 mL), saturated brine (1×100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrated residue was dried under high vacuum
  6. temperatureThe reaction mixture was heated at 100° C. for 2.5 h
  7. temperatureThe reaction mixture was cooled to room temperature
  8. customthe excess acetic acid was removed under vacuum
  9. customThe resulting residue was partitioned between water (100 mL) and ethyl acetate (200 mL)
  10. customThe organic layer was separated
  11. washwashed with saturated aqueous sodium bicarbonate (2×100 mL), saturated brine (1×100 mL)
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe concentrated residue was purified by flash chromatography on silica gel (eluting with 1:9 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-578e0d5e455642b1bb1d0ce2a6b2ab7d
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753344B2

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