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

HRID 6488

반응식

HRID 6488 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-(4-methoxybenzyloxy)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 and stir 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 (1st crop) and 0.15 g (2nd crop) of the title compound; mp 79°-80° C.

후처리

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

출처 및 근거

ORD 기록
ord-d099e8b2015d49a88b10fcd0cbfb9273
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248825

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