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Tributylphosphine → benzyl 3-cyano-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoate

HRID 922255
ノート
印刷プレビュー

反応式

HRID 922255 の反応式
[CH3:1][O:2][N:3]=[C:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.[C:21]([CH:23]([C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1)[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])#[N:22].C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:21]([CH:23]([C:35]1[CH:36]=[CH:37][C:38]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5]/[C:4](=[N:3]\[O:2][CH3:1])/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][CH:9]=2)=[CH:39][CH:40]=1)[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])#[N:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13831TributylphosphineHCID 66685080Benzyl 3-cyano-3-(4-hydroxyphenyl)propanoateHCID 866957602-(4-Hydroxymethyl-phenoxy)-1-phenyl-ethanone O-methyl-oxime

生成物 1

HCID 89790490benzyl 3-cyano-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoate収率 80.2%

試薬・触媒・溶媒 1

HCID 1140Toluene
溶媒

実験手順

To a 50 mL RB flask fitted with magnetic stirrer was charged Toluene (20 mL). To the stirred solvent was added 2-(4-Hydroxymethyl-phenoxy)-1-phenyl-ethanone O-methyl-oxime (0.039 g, 0.14 mmol) and benzyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.04 g, 0.14 mmol) at 0° C. for 5 min. Then added tributylphosphine (0.043 g, 0.2 mmol) stirred at 0° C. for 15 min, was added 1,1′aza(dicarbonyl)dipiperidine (0.054 g, 0.2 mmol), this resulting mass stirred at RT for 16 h. The solvent removed, the residue was extracted with ethyl acetate. The organic layer washed with water and brine solution and dried by anhydrous sodium sulphate to and evaporated, purified by 100-200 silica column using pet-ether and ethylacetate. The product obtained as a colourless oily liquid (0.06 g, 79.00%)

後処理

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. customThe solvent removed
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer washed with water and brine solution
  5. dry with materialdried by anhydrous sodium sulphate to and
  6. customevaporated
  7. custompurified by 100-200 silica column

出典と根拠

ORDレコード
ord-7f1e2ed957fc4f5681a8a9cfabe49e28
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278915B2

反応ノート

読み込み中…

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