HCID 57055398, compound → HCID 57058407, compound

HRID 1681001Notes

Reaction equation

HRID 1681001 reaction equation
[CH2:1]([O:8][C@@H:9]([C@@H:11]([O:13]CCCC)[CH3:12])[CH3:10])[C:2]1C=CC=[CH:4][CH:3]=1>C(O)C.Cl.[C].[Pd]>[CH2:1]([O:8][C@@H:9]([CH3:10])[C@H:11]([OH:13])[CH3:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Procedure

1.94 g of (2R,3S)-2-benzyloxy-3-butoxybutane was dissolved in a mixture of 80 ml of ethanol and 8 ml of 2 N hydrochloric acid. Thereto was added 200 mg of 5% palladium carbon. The mixture was subjected to hydrogenation at the atmospheric pressure at room temperature. After the completion of the reaction, the catalyst was removed by filtration and the filtrate was subjected to distillation. The residue was diluted with water and extracted with dichloromethane three times. The extract was dried and concentrated. The residue was subjected to Kugel-rohr distillation (30 mmHg) to obtain 0.76 g of (2R,3S)-3-butoxy-2-butanol. The 1H-NMR and IR spectrum of this compound were completely agreed with those of (2S,3R)-3-butoxy-2-butanol.

Workup

  1. customwas subjected to hydrogenation at the atmospheric pressure at room temperature
  2. customAfter the completion of the reaction
  3. customthe catalyst was removed by filtration
  4. distillationthe filtrate was subjected to distillation
  5. additionThe residue was diluted with water
  6. extractionextracted with dichloromethane three times
  7. customThe extract was dried
  8. concentrationconcentrated
  9. distillationThe residue was subjected to Kugel-rohr distillation (30 mmHg)

Sources & evidence

ORD record
ord-52580015ad07444d8aa01495fe85f965
Source dataset
uspto-grants-1992_12
Patent number
US05167863

Reaction notes

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