Tetrahydrofuran → 6-Diphenylphosphinomethyl-2,2'-bipyridine

HRID 2167169

반응식

HRID 2167169 반응식
Cl[P:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1COCC1.CC(C)([O-])C.[K+].Cl[CH2:27][C:28]1[N:33]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH:31]=[CH:30][CH:29]=1>CCOCC.O>[C:3]1([P:2]([CH2:27][C:28]2[N:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[CH:31]=[CH:30][CH:29]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 66180ChlorodiphenylphosphineHCID 6428432,2'-Bipyridine, 6-(chloromethyl)-HCID 23665647Potassium tert-butoxide

생성물 1

HCID 697902896-Diphenylphosphinomethyl-2,2'-bipyridine수율 61%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

Synthesis of the Ligand BPy-(Ph)PNN (10) An oven-dried 250 mL three-necked round bottom flask equipped with an argon inlet, a stirring bar, dropping funnel and one rubber septum was cooled under a stream of argon. The flask was then charged with chlorodiphenylphosphine (1.08 g, 6 mmol) in 30 mL dry ether. The solution was cooled to 0° C. and a THF solution (5 mL) of potassium tert-butoxide (74 mg, 6.6 mmol) was added dropwise via syringe during 10 min. The resulting brown coloured mixture was stirred for 1 hr at 0° C. and then a solution of 6-chloromethyl-2,2′-bipyridine (1.02 g, 5 mmol) in 20 mL dry ether was added dropwise (˜15 min) to it. The stirring was continued for a further 1 hr at the same temperature and the mixture was allowed to slowly warm up to room temperature and stirred overnight. To this reaction mixture was added 20 mL of degassed water and the ether phase was separated under N2 atmosphere. The aqueous phase was extracted with ether (2×20 mL). The combined ether solutions were dried over anhydrous Na2SO4, filtered under N2 pressure, and the solvent was removed under vacuum to get brownish-white solid. This was purified by column chromatography in the nitrogen glove box (basic alumina; hexane:ether (10:1) as eluent) to yield 1.08 g (61%) of 6-di-phenyphosphinomethyl-2,2′-bipyridine (BPy-(Ph)PNN) as a white crystalline solid.

후처리

  1. customequipped with an argon inlet, a stirring bar
  2. temperatureone rubber septum was cooled under a stream of argon
  3. waitThe stirring was continued for a further 1 hr at the same temperature
  4. temperatureto slowly warm up to room temperature
  5. stirringstirred overnight
  6. customthe ether phase was separated under N2 atmosphere
  7. extractionThe aqueous phase was extracted with ether (2×20 mL)
  8. dry with materialThe combined ether solutions were dried over anhydrous Na2SO4
  9. filtrationfiltered under N2 pressure
  10. customthe solvent was removed under vacuum
  11. customto get brownish-white solid
  12. customThis was purified by column chromatography in the nitrogen glove box (basic alumina; hexane:ether (10:1) as eluent)

출처 및 근거

ORD 기록
ord-a5ae0311d0dc4f40ae7160c72255e1d9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045381B2

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