Diethyl Ether → HCID 15525589、化合物

HRID 400291

反応式

HRID 400291 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 15525589HCID 15525589、化合物収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24f6624cf4964562acb0b8f826641599
出典データセット
uspto-grants-1998_10
特許番号
US05827501

関連ノート

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