Pentane → Di[(5-ethyl-2-ethylidene-[1,3]dioxan-5-yl)methyl]ether

HRID 983359ノート

反応式

HRID 983359 の反応式
CCCCC.[CH2:6]([C:8]1([CH2:16][O:17][CH2:18][C:19]2([CH2:27][CH3:28])[CH2:24][O:23][CH:22]([CH:25]=[CH2:26])[O:21][CH2:20]2)[CH2:13][O:12][CH:11]([CH:14]=[CH2:15])[O:10][CH2:9]1)[CH3:7]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Fe].C(N(CC)CC)C>[CH2:6]([C:8]1([CH2:16][O:17][CH2:18][C:19]2([CH2:27][CH3:28])[CH2:24][O:23][C:22](=[CH:25][CH3:26])[O:21][CH2:20]2)[CH2:13][O:12][C:11](=[CH:14][CH3:15])[O:10][CH2:9]1)[CH3:7]

参加物

5

反応物 2

HCID 8003PentaneHCID 11624015Di[(5-ethyl-2-vinyl-[1,3]dioxan-5-yl)methyl]ether

生成物 1

HCID 11602299Di[(5-ethyl-2-ethylidene-[1,3]dioxan-5-yl)methyl]ether収率 63.1%

試薬・触媒・溶媒 2

HCID 518773Pentacarbonyliron(0)触媒HCID 8471Triethylamine溶媒

実験手順

To 220 mL pentane in a 500 mL photochemical reactor was added 14.32 g (43.9 mmol) di[(5-ethyl-2-vinyl-[1,3]dioxan-5-yl)methyl]ether from the previous step. The solution was refluxed vigorously for 20 minutes to degas it, then 115 μL (171 μg, 0.87 μmol, 0.2 mol %) iron pentacarbonyl was added, and the solution refluxed for an additional 20 minutes. The resulting solution was irradiated for one hour, by when NMR showed no vinyl signals. After cooling to room temperature and the addition of 0.5 mL triethylamine, the solution was sparged with dry air for 4 hours. The pentane was removed by evaporation under reduced pressure, and the residual oil was distilled in a Kugelrohr apparatus (pot temperature 220° C., pressure 1-3 mbar) to give 9.04 g (63% yield) of di[(5-ethyl-2-ethylidene-[1,3]dioxan-5-yl)methyl]ether, 3, as a colorless oil. The identity of the product was confirmed by 1H NMR and mass spectra (observed: 363, 345, calculated for C18H35O7 (M+2H2O+H+): 363; calculated for C18H33O6 (M+H2O+H+): 345).

後処理

  1. temperatureThe solution was refluxed vigorously for 20 minutes
  2. customto degas it
  3. temperaturethe solution refluxed for an additional 20 minutes
  4. customThe resulting solution was irradiated for one hour, by when NMR
  5. customthe solution was sparged
  6. customwith dry air for 4 hours
  7. customThe pentane was removed by evaporation under reduced pressure
  8. distillationthe residual oil was distilled in a Kugelrohr apparatus (pot temperature 220° C., pressure 1-3 mbar)

出典と根拠

ORDレコード
ord-dce5633134b648ee978a7c685dcdb3c1
出典データセット
uspto-grants-2005_03
特許番号
US06863782B2

反応ノート

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