Acrylic Acid → 5-(Tetrahydro-pyran-2-yloxy)-pent-2-enoic acid

HRID 1887419

反応式

HRID 1887419 の反応式
[C:1]([OH:5])(=[O:4])C=C.[CH2:6]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:7][CH:8]=[CH2:9]>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.ClCCl>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[O:10][CH2:6][CH2:7][CH:8]=[CH:9][C:1]([OH:5])=[O:4]

参加物

5

反応物 2

HCID 6581Acrylic AcidHCID 3199452-But-3-enoxyoxane

生成物 1

HCID 668767525-(Tetrahydro-pyran-2-yloxy)-pent-2-enoic acid収率 84%

試薬・触媒・溶媒 2

HCID 178479819HCID 178479819、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

In a 500 ml rb flask were placed acrylic acid (2.85 g, 39.6 mmol) and Grubbs catalyst (1.68 g, 1.98 mmol) in anhydrous dichloromethane (200 ml). To this solution was added 2-but-3-enyloxy-tetrahydro-pyran (7.73 g, 49.50 mmol) and heated at refluxing for 12 hrs. The solvent was removed and the residue was purified on the column with Hexane/Ethyl acetate=100/5 to remove unchanged 2-but-3-enyloxy-tetrahydro-pyran. Then the column was eluted with Ethyl acetate/Methanol=100/1 to provide 6.66 g of a black oil (84%). 1H-NMR (DMSO-d6) δ 12.190 (s, 1H), 6.845-6.771 (m, 1H), 5.846-5.800 (d, 1H), 4.565-4.548 (t, 1H), 3.739-3.674 (m, 2H), 3.468-3.398 (m, 2H), 2.481-2.395 (m, 2H), 1.689-1.609 (m, 2H), 1.501-1.259 (m, 4H).

後処理

  1. customIn a 500 ml rb flask were placed
  2. temperatureheated
  3. temperatureat refluxing for 12 hrs
  4. customThe solvent was removed
  5. customthe residue was purified on the column with Hexane/Ethyl acetate=100/5
  6. customto remove unchanged 2-but-3-enyloxy-tetrahydro-pyran
  7. washThen the column was eluted with Ethyl acetate/Methanol=100/1

出典と根拠

ORDレコード
ord-4c8b41fda54f4171a5e9a5f897ddafa3
出典データセット
uspto-grants-2013_08
特許番号
US08501755B2

関連ノート

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