Hexane → HCID 69205838, 화합물

HRID 2378274노트

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HRID 2378274 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.CCCCCC.[N:24]1([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[CH:32]=[O:33])[CH:28]=[CH:27][CH:26]=[CH:25]1>C1COCC1.O>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([CH:32]([C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([N:24]3[CH:28]=[CH:27][CH:26]=[CH:25]3)[CH:30]=2)[OH:33])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH3:12]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 27765283-(1H-Pyrrol-1-yl)benzaldehydeHCID 217726904-Bromo-2-ethoxy-1-methoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 69205838HCID 69205838, 화합물수율 101.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-bromo-2-ethoxy-1-methoxy-benzene (1.5 g, 6.5 mmol) in THF (30 mL) was added a solution of n-butyllitium in hexane (2.4 mL, 2.5 N, 6.0 mmol) at −78° C. and kept for 20 min. To the mixture was added 3-pyrrol-1-yl-benzaldehyde (1.0 g, 5.8 mmol) at −78° C. After 18 h, water (30 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL) and dried over magnesium sulfate. Removal of solvent gave (3-ethoxy-4-methoxy-phenyl)-(3-pyrrol-1-yl-phenyl)-methanol (1.9 g, 100% crude yield). The sample was used in the next step without further purification.

후처리

  1. waitAfter 18 h
  2. customthe cold bath was removed
  3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent

출처 및 근거

ORD 기록
ord-ed6c95cbcb3547ff9199afcefc4a0677
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470723B2

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