p-Toluenesulfonic acid → 1-(6-Methyl-pyrid-3-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

HRID 2612

반응식

HRID 2612 반응식
[CH3:1][C:2]1[N:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.[CH3:20][C:21]1([CH3:33])[C:30]2[C:25](=[CH:26][C:27]([Br:31])=[CH:28][CH:29]=2)[C:24](=O)[CH2:23][CH2:22]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C(OCC)(=O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[C:27]([Br:31])[CH:26]=3)[C:21]([CH3:33])([CH3:20])[CH2:22][CH:23]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 12010205-Bromo-2-methylpyridineHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2회HCID 178418339Butyllithium

생성물 1

HCID 186200651-(6-Methyl-pyrid-3-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매2회

실험 절차

To a cold (-78° C.) solution of 6-methyl-3-bromopyridine (890 mg, 5.2 mmol) in THF (15 mL) was added n-BuLi in hexane (1.6M solution, 3.5 mL, 5.6 mmol) and stirred for 1 hour. This mixture was added to a flask containing 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A, 1.35 g, 5.4 mmol), in THF (5 mL) at -78° C. The reaction mixture was gradually warmed to ambient temperature and stirred for 16 hours. Thereafter it was diluted with ethyl acetate (100 mL), washed with water (10 mL), brine (10 mL) and dried with MgSO4. Solvent was removed by distillation, the crude material was dissolved in toluene (25 mL) and pTSA (530 mg, 2.8 mmol) was added. The mixture was heated at 90° C. for 36 hours. Thereafter it was diluted with ethyl acetate (100 mL), washed with 10% NaHCO3 (2×10 mL), brine (10 mL), dried with MgSO4 and the solvent was removed by evaporation. The title compound was obtained by recrystallization from ethyl acetate and hexane mixture (1:9).

후처리

  1. additionThis mixture was added to a flask
  2. customat -78° C
  3. stirringstirred for 16 hours
  4. washwashed with water (10 mL), brine (10 mL)
  5. dry with materialdried with MgSO4
  6. customSolvent was removed by distillation
  7. dissolutionthe crude material was dissolved in toluene (25 mL)
  8. temperatureThe mixture was heated at 90° C. for 36 hours
  9. washwashed with 10% NaHCO3 (2×10 mL), brine (10 mL)
  10. dry with materialdried with MgSO4
  11. customthe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-9920e201f1844369a4f53eaad2b0509b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728846

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