Dichloromethane → 2,3-Dihydrobenzofuran-5-carboxaldehyde

HRID 324605

反応式

HRID 324605 の反応式
ClCCl.[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1.[CH3:13][O:14]C(Cl)Cl>[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-].O>[O:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]=[O:14])=[CH:12][C:7]=2[CH2:6][CH2:5]1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 10329DihydrobenzofuranHCID 21004Methane, dichloromethoxy-

生成物 1

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde収率 61,555.602%

試薬・触媒・溶媒 2

HCID 160960Diamminetetrachlorotitanate(IV)触媒HCID 962Water溶媒

実験手順

Titanium chloride (28 ml) was dropwise added to a dichloromethane (100 ml) solution containing 2,3-dihydrobenzofuran (10.0 g, 83.2 mmols) and dichloromethyl methyl ether (11.3 ml, 0.125 mmols), while cooling with ice. The mixture was stirred for 1 hour, while still cooling with ice, and then water was added thereto. Dichloromethane was removed under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica-gel chromatography (hexane/ethyl acetate=1/1) to obtain 11.4 g (yield: 92%) of the target compound. This was oily.

後処理

  1. temperaturewhile cooling with ice
  2. temperaturewhile still cooling with ice
  3. customDichloromethane was removed under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified through silica-gel chromatography (hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-e60d3f4560d94190a849d10d23a90938
出典データセット
uspto-grants-2001_04
特許番号
US06218429B1

関連ノート

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