N-Methoxy-N-methylbenzamide → 1-Phenyl-3-[3-(4-methoxybenzyloxy)phenyl]-2-propyne-1-one

HRID 1757501

반응식

HRID 1757501 반응식
C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][O:12][C:13]1[CH:28]=[CH:27][C:16]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([C:25]#[CH:26])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1.CON(C)[C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[C:33]1([C:32](=[O:39])[C:26]#[C:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH2:17][C:16]3[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:28][CH:27]=3)[CH:20]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

5

반응물 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 152811221-Ethynyl-3-((4-methoxybenzyl)oxy)benzeneHCID 57426343Lithium bis(trimethylsilyl)amide

생성물 1

HCID 98409751-Phenyl-3-[3-(4-methoxybenzyloxy)phenyl]-2-propyne-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4methoxybenzyloxy)phenylacetylene (0.48 g, 2 mmol) in tetrahydrofuran and stir the brown solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenzamide (0.4 g, 2.4 mmol), remove the cooling bath andstir at room temperature for 1 hour. Partition the mixture between ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Filter through silica gel and elute with 10% ethyl acetate/hexane to yield a crude solid. Recrystallize (hexane, ethyl ether) to yield 0.26 g (lst crop) and 0.15 g (2nd crop) of the title compound; mp 79°-80 C.

후처리

  1. customPartition the mixture between ethyl ether and water
  2. customseparate the organic phase
  3. dry with materialdry (MgSO4)
  4. filtrationFilter
  5. customevaporate the solvent in vacuo
  6. customto yield an oil
  7. filtrationFilter through silica gel
  8. washelute with 10% ethyl acetate/hexane
  9. customto yield a crude solid
  10. customRecrystallize (hexane, ethyl ether)

출처 및 근거

ORD 기록
ord-48780852258f42e2936b931423a3798e
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05446068

연결된 노트

불러오는 중…