Water → HCID 21836624, 화합물

HRID 1740219노트

반응식

HRID 1740219 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])=[CH:4][CH:3]=1.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 11298348HCID 11298348, 화합물

생성물 1

HCID 21836624HCID 21836624, 화합물수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 184 mg (1.0 mmol) of 4-methyl-2'-hydroxy-1,1'-biphenyl (Example 12, Step C) in 3 mL of dimethylformamide was treated with 55 mg of 60% sodium hydride (33 mg NaH, 1.4 mmol). The reaction mixture was stirred at room temperature for 30 minutes then treated with 169 mg (1.19 mmol) of 1-fluoro-4-nitrobenzene. The reaction mixture was heated at 100° C. for 2 hours. The reaction mixture was cooled, poured into 50 mL of water and the resultant mixture was extracted with ethyl ether. The combined extracts were washed with water, dried over magnesium sulfate, filtered and evaporated under vacuum. The residue was chromatographed on silica, eluting with hexane/ethyl acetate (10:1) to give 271 mg (0.89 mmol,88%) of the product. FAB-MS: calculated for C19H15NO2 305: found 306 (M+H). 1H NMR (200 MHz,CDCl3): δ 2.28 (s,3H), 6.82 (d,2H), 7.19 (d,3H), 7.2-7.5 (m,5H), 8.05 (d,2H).

후처리

  1. temperatureThe reaction mixture was heated at 100° C. for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe resultant mixture was extracted with ethyl ether
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue was chromatographed on silica
  9. washeluting with hexane/ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-a1d28f438751483cae8afd93d00d418c
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968924

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