2-Chloropropane → 4-ISOPROPYLFURAN-2-CARBALDEHYDE

HRID 1363285ノート

反応式

HRID 1363285 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH:10]=[O:11].[CH:12](Cl)([CH3:14])[CH3:13]>C(=S)=S>[CH:12]([C:8]1[CH:7]=[C:6]([CH:10]=[O:11])[O:5][CH:9]=1)([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 63612-ChloropropaneHCID 7362FurfuralHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 122588064-ISOPROPYLFURAN-2-CARBALDEHYDE

試薬・触媒・溶媒 1

HCID 6348Carbon Disulfide溶媒

実験手順

To a suspension containing aluminium chloride (24 g, 180 mmol) in 100 mL of CS2 was added 2-furaldehyde (9.8 mL, 156 mmol). To this mixture was added dropwise isopropyl chloride (14.3 mL, 156 mmol), and the resulting mixture stirred at rt for 24 h. The dark mixture was carefully poured into a vigorously stirred 250 g of ice, and then extracted with ether (5×100 mL). The combined organic layers were washed with water, brine, dried (Na2SO4), filtered through a pad of silica gel, and concentrated. The residue was purified by flash chromatography (0-5% EtOAc in heptane) to give 4-isopropylfuran-2-carbaldehyde as an orange oil: Yield 3.5 g (16%). 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (d, J=6.88 Hz, 6H), 2.80-2.91 (m, 1H), 7.16-7.18 (m, 1H), 7.47 (q, J=0.91 Hz, 1H), 9.61 (d, J=0.59 Hz, 1H).

後処理

  1. extractionextracted with ether (5×100 mL)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-5% EtOAc in heptane)

出典と根拠

ORDレコード
ord-f8447c41b962472ea717289da12d6718
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

反応ノート

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