Methanol → 6-Bromo-4-tert-butyl-1,1-dimethyl-1,2-dihydronaphthalene

HRID 1381

반응식

HRID 1381 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.[C:15]([Mg]Cl)([CH3:18])([CH3:17])[CH3:16].CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH:8]=[C:9]2[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2회HCID 178418310HCID 178418310, 화합물

생성물 1

HCID 158960196-Bromo-4-tert-butyl-1,1-dimethyl-1,2-dihydronaphthalene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

In a flame dried round bottom flask 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G, 2.0 g, 7.93 mmol) was dissolved in anhydrous THF (50 ml) and 3,4,5,6,-tetrahydro-2(H)-pyrimidinone (DMPU) (11.5 ml, 95.16 mmol) was added, under argon atmosphere. The reaction was then cooled to -20° C. and a solution of t-butyl magnesium chloride (16 ml, 31.7 mmol) (2M in Et2O) was added dropwise and stirred at -20° C. for 2 h and at ambient temperature for 1 h, under argon atmosphere. The reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml) and extracted with EtOAc (2×50 ml). The combined extract was washed with water (20 ml), brine (20 ml) and dried over MgSO4. The solvent was evaporated under reduced pressure to afford a yellow oil. To this yellow oil were added MeOH (50 ml) and p-tolylsulfonic acid (100 mg). The resultant reaction solution was heated in an oil bath (60° C.) for 3 h. The reaction was cooled and quenched with water (20 ml), extracted with EtOAc (2×50 ml). The combined extract was washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml), and dried over MgSO4. The solvent was concentrated in vacuo and the title compound was obtained as a colorless oil after purification by flash chromatography (silica, hexane).

후처리

  1. customThe reaction was quenched at 0° C. with saturated ammonium chloride solution (20 ml)
  2. extractionextracted with EtOAc (2×50 ml)
  3. extractionThe combined extract
  4. washwas washed with water (20 ml), brine (20 ml)
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated under reduced pressure
  7. customto afford a yellow oil
  8. customThe resultant reaction solution
  9. temperaturewas heated in an oil bath (60° C.) for 3 h
  10. temperatureThe reaction was cooled
  11. customquenched with water (20 ml)
  12. extractionextracted with EtOAc (2×50 ml)
  13. extractionThe combined extract
  14. washwas washed with saturated NaHCO3 (20 ml), water (20 ml), brine (20 ml)
  15. dry with materialdried over MgSO4
  16. concentrationThe solvent was concentrated in vacuo

출처 및 근거

ORD 기록
ord-95296aadd2f34ea7a8a15d80c932bee0
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723666

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