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

HRID 1757510
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인쇄 미리보기

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HRID 1757510 반응식
C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][N:12]([CH3:29])[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:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[C:34]1([C:33](=[O:40])[C:26]#[C:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH2:17][C:16]3[CH:27]=[CH:28][C:13]([N:12]([CH3:11])[CH3:29])=[CH:14][CH:15]=3)[CH:20]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 193882263-(4-(Dimethylamino)benzyloxy)phenylacetyleneHCID 57426343Lithium bis(trimethylsilyl)amide

생성물 1

HCID 193882181-Phenyl-3-[3-(4-(dimethylamino)benzyloxy)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-(dimethylamino)benzyloxy)phenylacetylene (0.51 g, 2 mmol) in tetrahydrofuran and stir the 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. Purifyby silica gel chromatography to give the title compound. Alternatively, compounds of formula (1) can be prepared according to the procedure set forth in Scheme B, wherein all substituents, unless otherwise indicated, are previously described. ##STR3##

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

출처 및 근거

ORD 기록
ord-811a5c27251840fcad575856719bd0b2
출처 데이터셋
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05446068

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