Diethyl Ether → HCID 15525589, 화합물

HRID 1450046노트

반응식

HRID 1450046 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH2:6]([Li])[CH2:7][CH2:8][CH3:9].C([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)(=O)C1C=CC=CC=1.C(Cl)Cl.[CH2:28]([O:30]CC)C.[CH2:33](OCC)[CH3:34]>C1COCC1>[C:9]1([C:28]([C:23]2[CH:24]=[CH:19][N:20]=[CH:21][CH:22]=2)([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[OH:30])[CH:34]=[CH:33][CH:6]=[CH:7][CH:8]=1

참가 물질

7

반응물 5

HCID 3283Diethyl EtherHCID 70382-BenzoylpyridineHCID 8030ThiopheneHCID 21881112Ethyl ether methylene chlorideHCID 178418339Butyllithium

생성물 1

HCID 15525589HCID 15525589, 화합물수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Thiophene (1.150 g, 13.60 mmol) was dissolved in diethyl ether (50 mL, sodium benzophenone ketyl) under argon. n-Butyl lithium (5.10 mL, 13.60 mmol) was added quickly with a syringe under evolution of heat. The resulting mixture was stirred for 1 hour and 15 minutes at room temperature. After cooling to -75° C., benzoylpyridine (2.50 g, 13.6 mmol) dissolved in THF (10 mL) was added over a period of 10 minutes and the resulting mixture was stirred for 60 hours at room temperature. The resulting thick yellow suspension was diluted with THF (100 mL) and NaH2PO4 buffer (1.25M, 100 mL) was added. The organic layer was separated and washed with more NaH2PO4 buffer (2×30 mL, 1.25M), dried (Na2SO4) and evaporated yielding 3.24 g of crude material. Chromatography (flash, TLC gel 125 g, CH2Cl2 :diethyl ether 4:6) yielded 1.83 g (6.85 mmol, 50%) of the title compound.

후처리

  1. temperatureof heat
  2. temperatureAfter cooling to -75° C.
  3. additionwas added over a period of 10 minutes
  4. stirringthe resulting mixture was stirred for 60 hours at room temperature
  5. additionwas added
  6. customThe organic layer was separated
  7. washwashed with more NaH2PO4 buffer (2×30 mL, 1.25M)
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customyielding 3.24 g of crude material

출처 및 근거

ORD 기록
ord-4125e1d845e84211babb76cd0a616987
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599522

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