Hexane → HCID 69205838、化合物

HRID 2378274ノート

反応式

HRID 2378274 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 69205838HCID 69205838、化合物収率 101.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed6c95cbcb3547ff9199afcefc4a0677
出典データセット
uspto-grants-2008_12
特許番号
US07470723B2

反応ノート

読み込み中…