1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 5-vinyl-1,3-dioxane-5-carboxylate

HRID 2176246ノート

反応式

HRID 2176246 の反応式
S(O[CH:12]([C:14]1([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][O:18][CH2:17][O:16][CH2:15]1)[CH3:13])(C1C=CC(C)=CC=1)(=O)=O.C1CCN2C(=NCCC2)CC1>CCOCC>[CH2:23]([O:22][C:20]([C:14]1([CH:12]=[CH2:13])[CH2:19][O:18][CH2:17][O:16][CH2:15]1)=[O:21])[CH3:24]

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86706084Ethyl 5-(1-(tosyloxy)ethyl)-1,3-dioxane-5-carboxylate

生成物 1

HCID 85877288Ethyl 5-vinyl-1,3-dioxane-5-carboxylate収率 33.3%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
140 °C

実験手順

A mixture of ethyl 5-(1-(tosyloxy)ethyl)-1,3-dioxane-5-carboxylate (20.7 g, 58 mmol) and DBU (25 mL) was heated at 140° C. for 3 h. After being cooled to rt, the reaction mixture was poured into ether (300 mL), and the organic layer was washed with brine (3×). The ether layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with petroleum ether/ether 30:1 to 20:1 to give a crude product, which was distilled under reduced pressure (45-49° C./0.3 mbar) to afford the title compound (3.6 g, 33%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.29 (t, J=11.0 Hz, 3H), 3.70 (d, J=11.6 Hz, 2H), 4.25 (t, J=7.2 Hz, 2H), 4.44 (t, J=11.2 Hz, 2H), 4.71 (d, J=8.0 Hz, 1H), 4.95 (d, J=6.0 Hz, 1H), 5.24 (m, 1H), 5.27 (m, 1H), 5.65 (m, 1H). This 1H spectral data is in good agreement with that reported for the synthesis of the title compound, the which is described in Borremans, F. et al. Bull. Soc. Chim. Belg. 1976, 85, 681-696.

後処理

  1. temperatureAfter being cooled to rt
  2. washthe organic layer was washed with brine (3×)
  3. dry with materialThe ether layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with petroleum ether/ether 30:1 to 20:1
  7. customto give a crude product, which
  8. distillationwas distilled under reduced pressure (45-49° C./0.3 mbar)

出典と根拠

ORDレコード
ord-4b40dbc985204ac08b3806be128ca50c
出典データセット
uspto-grants-2015_06
特許番号
US09062092B2

反応ノート

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