Water → HCID 57055398, compound

HRID 1681000Notes

Reaction equation

HRID 1681000 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:13])[C@@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:16](I)[CH2:17][CH2:18][CH3:19].O>CN(C)C=O>[CH2:1]([O:8][C@@H:9]([C@@H:10]([O:12][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:11])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 12695196HCID 12695196, compound

Product 1

HCID 57055398HCID 57055398, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.90 g of (2S,3R)-3-benzyloxy-2-butanol was dissolved in 50 ml of dry N,N-dimethylformamide. Thereto was added in small portions 2.53 g of about 60% oily sodium hydride. The mixture was stirred for 1 hour at room temperature. 11.63 g of butyl iodide was dropped with ice cooling. The mixture was stirred overnight at room temperature. The reaction mixture was poured into water. The resulting mixture was extracted with ether three times. The extract was washed with water three times, dried and concentrated. The residue was subjected to Kugel-rohr distillation (1 mmHg) to obtain 2.05 g of (2R,3S)-2-benzyloxy-3butoxybutane.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionThe resulting mixture was extracted with ether three times
  3. washThe extract was washed with water three times
  4. customdried
  5. concentrationconcentrated
  6. distillationThe residue was subjected to Kugel-rohr distillation (1 mmHg)

Sources & evidence

ORD record
ord-f58b4adeb25b48bb87ba338ba46397f1
Source dataset
uspto-grants-1992_12
Patent number
US05167863

Reaction notes

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