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Triphenylphosphine → Ethyl (2R)-2-{4-[5-methyl-1-(4-octyloxyphenyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate

HRID 1072754
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HRID 1072754 반응식
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:8]=2)[C:5]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.O[C@@H:30]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]([O:33][CH2:34][CH3:35])=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:12]=2)[C:5]([C:22]2[CH:23]=[CH:24][C:25]([O:28][C@H:30]([CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:26][CH:27]=2)=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9877619Ethyl phenyllactate, (-)-HCID 223876094-[5-methyl-1-(4-octyloxyphenyl)-1H-pyrrol-2-yl]phenol

생성물 1

HCID 86588900Ethyl (2R)-2-{4-[5-methyl-1-(4-octyloxyphenyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate수율 39.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a solution of 4-[5-methyl-1-(4-octyloxyphenyl)-1H-pyrrol-2-yl]phenol (740 mg, 1.96 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (570 mg, 2.94 mmol) and triphenylphosphine (770 mg, 2.94 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (741 mg, 2.94 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 420 mg (yield: 39.6%)

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate anhydride
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)
  5. customto give the object compound as an oily substance

출처 및 근거

ORD 기록
ord-73a7679c640c4619a273cd2828e981e1
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06911468B2

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