Ethanol → 2-Bornanecarboxylic acid

HRID 1198008ノート

反応式

HRID 1198008 の反応式
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[CH2:13]([OH:15])C.[CH:16]1[CH:21]=CC(CO[C@H]2C(OCC3C=CC=CC=3)[C@@H](OCC3C=CC=CC=3)[C@H](O)C(O)[C@H]2O)=C[CH:17]=1>[Pd].O>[C:2]12([CH3:12])[C:16]([CH3:21])([CH3:17])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]2[C:13]([OH:15])=[O:1]

参加物

6

反応物 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 30355961,5,6-Tri-O-benzylmyoinositol

生成物 1

HCID 5655942-Bornanecarboxylic acid

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

実験手順

The formed substance, 3,4-di-O-allyl-5,6-di-O-benzyl-myo-inositol (12.1 g) together with dibutylin oxide (4.0 g) and dry benzene (150 ml) was heated under reflux for 2 hours. After evaporation of benzene and addition of dry dimethyl formamide (60 ml) and benzyl bromide (5.5 ml) the solution was kept at 50° C. for 24 hours. The crude product was chromatographed on silica gel (250 g) and eluted with ether-light petroleum to give 9.5 g of 1,5,6-tri-O-benzyl-3,4-di-O-allyl-myo-inositol. A mixture of the obtained product, toluene-p-sulphonic acid monohydrate (0.9 g), ethanol (190 ml), water (10 ml) and palladium-on-charcoal (1 g, 10% from Fluka) was heated under reflux with stirring for 4 hours. The crude product was chromatographed on silica gel and elution with ether-light petroleum (4:1) gave a compound, identified with NMR to be 1,5,6-tri-O-benzyl-myo-inositol. The described substances are racemic mixtures. If desired the racemic mixture of the latter one could be separated into the enantiomeric forms by forming diastereomers with camphanic acid.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe crude product was chromatographed on silica gel and elution with ether-light petroleum (4:1)
  4. customgave a compound
  5. additionthe racemic mixture of the latter one
  6. customcould be separated into the enantiomeric forms

出典と根拠

ORDレコード
ord-9cdec1d2cf8146ee973310751ebaf883
出典データセット
uspto-grants-1994_01
特許番号
US05278332

反応ノート

読み込み中…