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

HRID 1977511노트

반응식

HRID 1977511 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-92f5d6271eb04cd1b57416137c0b4596
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06232476B1

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