Cesium carbonate → 4-(2',6'-Dimethoxyphenyl)-2-nitrobenzyl alcohol

HRID 2185946

反応式

HRID 2185946 の反応式
[N+:1]([C:4]1[CH:11]=[C:10](Cl)[CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:16]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].P(C1CCCCC1)(C1CCCCC1)C1CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:16]=1[C:10]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 899564-Chloro-2-nitrobenzyl alcoholHCID 2734343(2,6-Dimethoxyphenyl)boronic acid

生成物 1

HCID 700560064-(2',6'-Dimethoxyphenyl)-2-nitrobenzyl alcohol

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5.0 g (26.7 mmol) of 2-nitro-4-chlorobenzyl alcohol, 6.33 g (34.8 mmol) of 2,6-dimethoxybenzene boronic acid, 0.73 g (0.80 mmol) of Pd2dba3, 11.3 g (34.8 mmol) of Cs2CO3, and 0.45 g (1.60 mmol) of Cy3P was dissolved in 100 mL of dioxane and warmed to reflux for 18 h. The reaction mixture was cooled, filtered through a pad of silica gel which was washed with Et2O and concentrated. The residue was purified by flash column chromatography on silica gel eluted with a gradient of 25-50% Et2O in hexanes and gave 4-(2′,6′-dimethoxyphenyl)-2-nitrobenzyl alcohol as a pale yellow solid.

後処理

  1. temperaturewarmed
  2. temperatureto reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through a pad of silica gel which
  5. washwas washed with Et2O
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluted with a gradient of 25-50% Et2O in hexanes

出典と根拠

ORDレコード
ord-8bf5fae181a84a2da0e6ddfa8142ed82
出典データセット
uspto-grants-2002_06
特許番号
US06403584B1

関連ノート

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