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Toluene → 2-(4-Cyclopropyl-2,6-dimethyl-phenyl)-4-(tetrahydropyran-4-ylmethyl)-cyclopentane-1,3-dione

HRID 509173
ノート
印刷プレビュー

反応式

HRID 509173 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]2=[O:22])=[C:4]([CH3:23])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:32]1(B(O)O)[CH2:34][CH2:33]1.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(COC)OC>[CH:32]1([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]3[C:13](=[O:14])[CH:12]([CH2:15][CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[CH2:11][C:10]3=[O:22])=[C:4]([CH3:23])[CH:3]=2)[CH2:34][CH2:33]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 584814642-(4-Bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

生成物 1

HCID 584815142-(4-Cyclopropyl-2,6-dimethyl-phenyl)-4-(tetrahydropyran-4-ylmethyl)-cyclopentane-1,3-dione収率 13.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
130 °C

実験手順

A mixture of 2-(4-bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione (0.1 g, 0.26 mmol), potassium phosphate (0.11 g, 0.53 mmol), cyclopropyl boronic acid (0.09 g, 1.05 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.06 g, 0.053 mmol), toluene (2 ml), dimethoxyethane (0.5 ml) and water (0.5 ml) is heated under microwave conditions at 130° C. for 22 minutes. The organic solvent is evaporated under vacuo, diluted with water and extracted with ethylacetate (3×25 ml). The combined organic extracts are combined, washed with water and brine, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel followed by preparative HPLC to give 2-(4-cyclopropyl-2,6-dimethyl-phenyl)-4-(tetrahydropyran-4-ylmethyl)-cyclopentane-1,3-dione (0.012 g).

後処理

  1. customThe organic solvent is evaporated under vacuo
  2. additiondiluted with water
  3. extractionextracted with ethylacetate (3×25 ml)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-34a7c39a85b44dda8cd278f930f21ca4
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096560B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート