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

HRID 922255
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HRID 922255 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene
용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-7f1e2ed957fc4f5681a8a9cfabe49e28
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278915B2

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