Iodine → 2-(4,4-Dimethyl-2-oxazolin-2-yl)-4'-n-butylbiphenyl

HRID 483283

반응식

HRID 483283 반응식
[Mg].CO[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=1.II.BrC(Br)C.I[CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.IC1C=CC(CCCC)=CC=1>O1CCCC1.O>[CH3:15][C:13]1([CH3:16])[CH2:12][O:11][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:31]2[CH:32]=[CH:33][C:28]([CH2:27][CH2:26][CH2:25][CH3:24])=[CH:29][CH:30]=2)=[N:14]1

참가 물질

9

반응물 6

HCID 807IodineHCID 112011,1-DibromoethaneHCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 27246071-Butyl-4-iodobenzeneHCID 5462224MagnesiumHCID 12709818(4-Iodobutyl)benzene

생성물 1

HCID 136292792-(4,4-Dimethyl-2-oxazolin-2-yl)-4'-n-butylbiphenyl수율 25%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A mechanically stirred solution of magnesium turnings (Mallinckrodt, for Grignard's reaction, 3.75 g., 0.154 mole) and 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (30 g, 0.146 mole) in 50 mL dry tetrahydrofuran under nitrogen was prepared. To this was added a crystal of iodine, 1 mL of dibromoethane and 2 mL of neat p-Iodo n-butylbenzene to initiate the Grignard reaction. After warming to initiate the reaction, the remainder of the p-iodo-n-butylbenzene (40 g, 0.154 mole) in 50 mL dry tetrahydrofuran was added dropwise at a rate sufficient to maintain the reaction at gentle reflux. The addition took 1 hr and the reaction mixture was then heated at reflux for 3 hr. The reaction was then cooled to room temperature and 15 mL water was added dropwise to coagulate the salts. The tetrahydrofuran was decanted and the remaining solids were slurried twice with 200 mL ethyl ether and twice with 300 mL dichloromethane. Each organic extract was decanted from the solids in turn and combined and evaporated under reduced pressure to an oil. The oil was redissolved in 300 mL dichloromethane, washed once with 100 ml saturated sodium chloride solution, dried and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (0.027 Torr, 130°) to yield 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-n-butylbiphenyl as an oil, yield 25%.

후처리

  1. customthe Grignard reaction
  2. temperatureAfter warming
  3. customthe reaction
  4. temperatureto maintain
  5. customthe reaction at gentle reflux
  6. additionThe addition
  7. temperaturethe reaction mixture was then heated
  8. temperatureat reflux for 3 hr
  9. customThe tetrahydrofuran was decanted
  10. extractionEach organic extract
  11. customwas decanted from the solids in turn
  12. customevaporated under reduced pressure to an oil
  13. dissolutionThe oil was redissolved in 300 mL dichloromethane
  14. washwashed once with 100 ml saturated sodium chloride solution
  15. customdried
  16. concentrationconcentrated under reduced pressure
  17. distillationThe resulting residue was distilled under reduced pressure (0.027 Torr, 130°)

출처 및 근거

ORD 기록
ord-72ecc216163440898323f1a262f06853
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04578522

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