Acetonitrile → (3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanone

HRID 583478노트

반응식

HRID 583478 반응식
CON(C)[C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC#N>CCOCC>[CH:14]1([O:13][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=2[O:11][CH3:12])[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH2:15][CH2:16][CH2:17][CH2:18]1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 21187934HCID 21187934, 화합물HCID 178418255HCID 178418255, 화합물

생성물 1

HCID 10827779(3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To an ice bath cooled stirred solution of N-methoxy-N-methyl-3-cyclopentoxy-4-methoxybenzamide (1.2 g, 4.3 mmol) in 15 mL of anhydrous ether was added a 3 M solution of phenylmagnesium bromide (3.6 mL, 10.8 mmol) in ether dropwise over a 20 minute period. A white gum precipitated from the mixture and dry THF (6 mL) was added to facilitate stirring. The reaction mixture was allowed to warm to room temperature and was stirred for 4 hours. The reaction was then quenched at 0° C. with a saturated aqueous solution of ammonium chloride (8 mL). The resulting mixture was allowed to warm to room temperature and was diluted with ethyl acetate (10 mL). The organic layer was separated and sequentially washed with 1 N citric acid (2×10 mL), saturated NaHCO3(aq) (2×10 mL), and brine (2×10 mL). The organic layer was then dried over MgSO4, filtered and concentrated in vacuo to give a viscous oil. The crude product was purified by flash column chromatography (silica gel, methylene chloride) and the resulting product was then dried in vacuo (40° C., <1 mmHg) to afford 0.75 g (60%) of a slightly impure product as a white solid: mp 73.5-75.0° C.; 1H NMR (CDCl3) δ 7.80-7.72 (m, 2H), 7.63-7.15 (m, 5H), 6.94-6.79 (m, 1H), 4.91-4.78 (m, 1H), 3.92 (s, 3H), 2.09-1.50 (m, 8H) also some impurity in the aromatic region; 13C NMR (CDCl3) δ 195.7, 153.9, 147.5, 138.3, 131.8, 129.7, 128.1, 125.1, 120.3, 115.5, 110.3, 80.5, 56.1, 32.7, 24.1; HPLC (Waters Nova-Pak/C18 column, 3.9×150mrn, 4 micron, 1 mL/min, 60/40, CH3CN/0.1% H3PO4(aq)) 6.2, min 99%.

후처리

  1. temperatureTo an ice bath cooled
  2. customA white gum precipitated from the mixture and dry THF (6 mL)
  3. additionwas added
  4. stirringwas stirred for 4 hours
  5. customThe reaction was then quenched at 0° C. with a saturated aqueous solution of ammonium chloride (8 mL)
  6. temperatureto warm to room temperature
  7. additionwas diluted with ethyl acetate (10 mL)
  8. customThe organic layer was separated
  9. washsequentially washed with 1 N citric acid (2×10 mL), saturated NaHCO3(aq) (2×10 mL), and brine (2×10 mL)
  10. dry with materialThe organic layer was then dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto give a viscous oil
  14. customThe crude product was purified by flash column chromatography (silica gel, methylene chloride)
  15. customthe resulting product was then dried in vacuo (40° C., <1 mmHg)
  16. customto afford 0.75 g (60%) of a slightly impure product as a white solid

출처 및 근거

ORD 기록
ord-496a703d8aba4da99a3df98f1fe49277
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929117

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