2-Bromomesitylene → HCID 68808338, 화합물

HRID 272594

반응식

HRID 272594 반응식
BrC1C(C)=CC(C)=CC=1C.[Li]C(C)(C)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.CON(C)[C:27]([CH:29]1[CH2:33][CH:32]=[CH:31][CH2:30]1)=[O:28]>C1COCC1.CCCCC>[CH2:32]1[CH2:31][CH:30]=[C:29]([C:27]([C:23]2[C:18]([O:17][CH3:16])=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:28])[CH2:33]1

참가 물질

7

반응물 4

HCID 684732-BromomesityleneHCID 742012-MethoxypyridineHCID 12990999HCID 12990999, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 68808338HCID 68808338, 화합물

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

Bromo-2,4,6-trimethylbenzene (16.9 g, 85 mmol) was stirred in anhydrous THF (340 mL) at −78° C. under nitrogen and treated with t-BuLi (100 mL of 1.7 M soln. in pentane, 170 mmol) dropwise via an addition funnel over 30 min. A yellow slurry forms and is stirred 1 h. To this was added 2-methoxypyridine (8.45 g, 77.3 mmol) in anhydrous THF (10 mL) over 5 min. The mixture was allowed to warm to 0° C. and stirred for 1 h, then at ambient temperature for 1 h, then recooled to −78° C. and treated with cyclopent-3-enecarboxylic acid methoxy-methyl-amide (12.4 g, 80 mmol) in anhydrous THF (20 mL) over 5 min. The resulting mixture was stirred 18 h (the bath evaporated and the mixture achieved ambient temperatures). The mixture was poured into saturated aqueous NaHCO3 solution (250 mL) and stirred 20 min. The mixture was extracted with Et2O (3×100 mL). The organic layer was washed with H2O (2×100 mL) and saturated aqueous NaCl solution then dried over Na2SO4, filtered and concentrated to an oil (26 g). Purification by chromatography on silica gel eluting first with hexane to remove mesitylene followed by 10% then 20% Et2O/hexanes elutes product, which was concentrated to a clear oil (12.2 g, 75% crude). (TLC 10% Et2O/hexanes Rf 0.36); 1H NMR (400 MHz, CDCl3) δ 8.28 (dd, J=4.9, 2.0 Hz, 1H), 8.02 (m, 1H), 6.97 (m, 1H), 5.65 (s, 2H), 4.03 (s, 3H), 4.17, (m, 1H), 2.67 (m, 4H); GCMS m/z 203 (M)+.

후처리

  1. stirringstirred for 1 h
  2. waitat ambient temperature for 1 h
  3. customrecooled to −78° C.
  4. stirringThe resulting mixture was stirred 18 h (the bath
  5. customevaporated
  6. additionThe mixture was poured into saturated aqueous NaHCO3 solution (250 mL)
  7. stirringstirred 20 min
  8. extractionThe mixture was extracted with Et2O (3×100 mL)
  9. washThe organic layer was washed with H2O (2×100 mL) and saturated aqueous NaCl solution
  10. dry with materialthen dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated to an oil (26 g)
  13. customPurification by chromatography on silica gel eluting first with hexane
  14. customto remove mesitylene
  15. concentration20% Et2O/hexanes elutes product, which was concentrated to a clear oil (12.2 g, 75% crude)

출처 및 근거

ORD 기록
ord-b53f19f45fb84be3a9d7a7d7d5c327cd
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456177B2

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