Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 3-[2-(4-Benzyloxy-benzoyl)-5-methoxy-phenyl]-1-phenyl-propan-1-one

HRID 1977511ノート

反応式

HRID 1977511 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:16]CCO1.[Li]CCCC.[CH2:28]([O:35][C:36]1[CH:43]=[CH:42][C:39]([C:40]#N)=[CH:38][CH:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC1C=CC(S([O-])(=O)=[O:52])=CC=1.C1C=C[NH+]=CC=1>C1COCC1.CC(C)=O.O>[CH2:28]([O:35][C:36]1[CH:43]=[CH:42][C:39]([C:40]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[CH2:10][CH2:11][C:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])=[O:52])=[CH:38][CH:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

8

反応物 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5613714-BenzyloxybenzonitrileHCID 98638172-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolaneHCID 178418339Butyllithium

生成物 1

HCID 98683843-[2-(4-Benzyloxy-benzoyl)-5-methoxy-phenyl]-1-phenyl-propan-1-one収率 236.8%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of 2-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolane (0.9 g, 2.5 mmol) in 10 ml of dry THF was cooled to −78° C. and n-BuLi (2.5 M in hexane, 1 ml) was added dropwise. The solution was stirred at −78° C. for 2 h and 4-benzyloxy-benzonitrile (0.575 g, 2.75 mmol) in 2 ml of THF was added. The mixture was allowed to warm to room temperature and refluxed overnight. The solution was then quenched with sat. NH4Cl and the solvent was evaporated. A solution of the residue in 20 ml of wet acetone, 5 ml of H2O containing PPTS (188 mg, 0.75 mmol) was refluxed overnight. Regular workup and column purification afforded an unoptimized weight of 0.8 g 3-[2-(4-Benzyloxy-benzoyl)-5-methoxy-phenyl]-1-phenyl-propan-1-one.

後処理

  1. temperatureto warm to room temperature
  2. temperaturerefluxed overnight
  3. customThe solution was then quenched with sat. NH4Cl
  4. customthe solvent was evaporated
  5. temperaturewas refluxed overnight
  6. customRegular workup and column purification

出典と根拠

ORDレコード
ord-92f5d6271eb04cd1b57416137c0b4596
出典データセット
uspto-grants-2001_05
特許番号
US06232476B1

反応ノート

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