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Cesium carbonate → 3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole

HRID 2423520
ノート
印刷プレビュー

反応式

HRID 2423520 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]1([CH3:22])[C:12]([CH3:14])([CH3:13])[O:11][B:10]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[O:9]1.Cl[CH2:24][C:25]1[C:26]([C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:40])=[N:27][O:28][C:29]=1[CH:30]([CH3:32])[CH3:31]>CN(C)C=O>[Cl:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:40])[C:33]=1[C:26]1[C:25]([CH2:24][O:21][C:18]2[CH:19]=[CH:20][C:15]([B:10]3[O:9][C:8]([CH3:22])([CH3:7])[C:12]([CH3:13])([CH3:14])[O:11]3)=[CH:16][CH:17]=2)=[C:29]([CH:30]([CH3:32])[CH3:31])[O:28][N:27]=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

5

反応物 3

HCID 10796Cesium carbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

生成物 1

HCID 597090393-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole収率 80%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
60 °C

実験手順

Cesium carbonate (1.96 g, 6.03 mmol) was added to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (1.26 g, 5.74 mmol) and 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole (1.75 g, 5.74 mmol) in N,N-dimethylformamide (57 mL) at room temperature. The resulting suspension was heated for sixty-nine hours at 60° C. The reaction was cooled and concentrated to remove the N,N-dimethylformamide, then water was added and the reaction mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:6 ethyl acetate:hexanes to give 2.24 g (80%) of 3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole as an solid. 1H NMR (400 MHz, d6-DMSO): δ 7.62-7.59 (m, 2H), 7.55-7.48 (m, 3H), 6.76 (d, J=9 Hz, 2H), 4.82 (s, 2H), 3.44 (septet, J=7 Hz, 1H), 1.31 (d, J=7 Hz, 6H), 1.24 (s, 12H). ESI-LCMS m/z 488 (M+H)+.

後処理

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customto remove the N,N-dimethylformamide
  4. additionwater was added
  5. extractionthe reaction mixture was extracted with diethyl ether
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 1:6 ethyl acetate

出典と根拠

ORDレコード
ord-86d8b31279e8427da327036d926fa1a5
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07960552B2

反応ノート

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