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Ethyl isobutyrate → 2,2-Dimethyl-3-[4-(3-pyridylmethyl)phenyl]propionic acid ethyl ester

HRID 1680027
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HRID 1680027 반응식
[CH:1]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.C(OCC)(=O)C(C)C.[CH2:29]([O:31][C:32](=[O:50])/[C:33](/[CH2:48]C)=[CH:34]/[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)=[CH:37][CH:36]=1)[CH3:30].[Cl-].[NH4+]>O1CCCC1.CCCCCC.CN(P(N(C)C)(N(C)C)=O)C>[CH2:29]([O:31][C:32](=[O:50])[C:33]([CH3:48])([CH3:1])[CH2:34][C:35]1[CH:36]=[CH:37][C:38]([CH2:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)=[CH:39][CH:40]=1)[CH3:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 6

HCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 12904571(E)-2-Ethyl-3-[4-(3-pyridylmethyl)phenyl]acrylic acid ethyl esterHCID 178418339Butyllithium

생성물 1

HCID 54391330
2,2-Dimethyl-3-[4-(3-pyridylmethyl)phenyl]propionic acid ethyl ester

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매HCID 12679Hexamethylphosphoramide용매

실험 절차

To a 3.0 M solution of lithium diisopropylamide in tetrahydrofuran [prepared from diisopropylamine (0.56 ml), tetrahydrofuran (5 ml) and a 1.4 M solution of butyllithium in hexane (2.2 ml)] was added dropwise 0.41 ml of ethyl isobutyrate at -70° C., and the mixture was stirred at that temperature for 40 minutes. To it was added dropwise a solution of 0.26 g of the benzyl chloride compound (prepared as described in Reference Example 2) in 2.8 ml of a mixture of HMPA and tetrahydrofuran (1:1) at -70° C., and the mixture was stirred at that temperature for 2 hours, and then at room temperature for one hour. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 0.27 g of the title compound having the following physical characteristics:

후처리

  1. stirringthe mixture was stirred at that temperature for 2 hours
  2. waitat room temperature for one hour
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

출처 및 근거

ORD 기록
ord-c926500ccd484dbc938445013593a5c8
출처 데이터셋
uspto-grants-1981_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04271170

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