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

HRID 6488

反応式

HRID 6488 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d099e8b2015d49a88b10fcd0cbfb9273
出典データセット
uspto-grants-1993_09
特許番号
US05248825

関連ノート

読み込み中…