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

HRID 553279
ノート
印刷プレビュー

反応式

HRID 553279 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒
HCID 167845
palladium(II) acetate
触媒
HCID 1140Toluene溶媒

実験手順

[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).

後処理

  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]

出典と根拠

ORDレコード
ord-afa6b8abe1114c1ab5991068c3143061
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951954B2

反応ノート

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