Sodium Methoxide → Spiro[2.5]octane-5,7-dione

HRID 1503077ノート

反応式

HRID 1503077 の反応式
CO[C:3](=[O:12])[CH2:4][C:5]1([CH2:8][C:9](=[O:11])[CH3:10])[CH2:7][CH2:6]1.C[O-].[Na+]>O1CCCC1.CO.C(OC)(C)(C)C>[CH2:6]1[C:5]2([CH2:4][C:3](=[O:12])[CH2:10][C:9](=[O:11])[CH2:8]2)[CH2:7]1

参加物

6

反応物 2

HCID 10942334Sodium MethoxideHCID 73052801HCID 73052801、化合物

生成物 1

HCID 55264674Spiro[2.5]octane-5,7-dione

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

23.3 g of crude [1-(2-oxo-propyl)-cyclopropyl]-acetic acid methyl ester (60% purity, from step 5) are dissolved in 135 ml of tetrahydrofuran and 17.1 g of a sodium methanolate solution in methanol (30% in methanol) are added at room temperature and the mixture is stirred for six hours. Then the solution is diluted with 135 ml of methyl tert-butyl ether and quenched with 135 ml of water. Stirring is continued for five minutes, then the phases are separated. The aqueous phase is extracted with 67.5 ml of methyl tert-butyl ether, then acidified to pH 2-3 with 37% HCl and washed twice with 67.5 ml of methyl tert-butyl ether each. The combined organic phases are washed with 18 ml of water and concentrated to dryness. The crude product is stirred with 18 ml of cold methyl tert-butyl ether and then the precipitate is isolated by filtration. The filter cake is washed with 18 ml of cold methyl tert-butyl ether to yield the product as an off-white solid.

後処理

  1. customquenched with 135 ml of water
  2. stirringStirring
  3. waitis continued for five minutes
  4. customthe phases are separated
  5. extractionThe aqueous phase is extracted with 67.5 ml of methyl tert-butyl ether
  6. washwashed twice with 67.5 ml of methyl tert-butyl ether each
  7. washThe combined organic phases are washed with 18 ml of water
  8. concentrationconcentrated to dryness
  9. stirringThe crude product is stirred with 18 ml of cold methyl tert-butyl ether
  10. customthe precipitate is isolated by filtration
  11. washThe filter cake is washed with 18 ml of cold methyl tert-butyl ether

出典と根拠

ORDレコード
ord-69be6c9dfdbc466a96139ac8d15eabdc
出典データセット
uspto-grants-2015_12
特許番号
US09212120B2

反応ノート

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