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Allyl Alcohol → Tert-butyl 2,6-dichlorophenethyl(3-(3-oxopropyl)benzyl)carbamate

HRID 553279
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HRID 553279 반응식
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:16][CH2:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH2:32]([OH:35])[CH:33]=[CH2:34]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:16][CH2:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:34][CH2:33][CH:32]=[O:35])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

7

반응물 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 67165818[2-(2,6-Dichloro-phenyl)-ethyl]-(3-iodo-benzyl)-carbamic acid tert-butyl ester

생성물 1

HCID 86628371Tert-butyl 2,6-dichlorophenethyl(3-(3-oxopropyl)benzyl)carbamate

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매
HCID 167845
palladium(II) acetate
촉매
HCID 1140Toluene용매

실험 절차

[2-(2,6-Dichloro-phenyl)-ethyl]-(3-iodo-benzyl)-carbamic acid tert-butyl ester (506 mg), tetrabutylammonium chloride (280 mg), sodium bicarbonate (210 mg), allyl alcohol (100 μL) and toluene (20 mL) were charged to a flask, followed by palladium acetate (10 mg) and the resultant mixture heated to 80° C., under nitrogen for 5 hours. On cooling, the reaction was filtered, the filtrate diluted with toluene and extracted sequentially, twice with water, once with brine, dried (magnesium sulfate) and evaporated. Purification on silica, eluting with a gradient of iso-hexane/ethyl acetate [4:1 to 2:1], gave the subtitle product as an oil (300 mg).

후처리

  1. temperatureOn cooling
  2. filtrationthe reaction was filtered
  3. additionthe filtrate diluted with toluene
  4. extractionextracted sequentially, twice with water, once with brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customPurification on silica
  8. washeluting with a gradient of iso-hexane/ethyl acetate [4:1 to 2:1]

출처 및 근거

ORD 기록
ord-afa6b8abe1114c1ab5991068c3143061
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951954B2

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