1-Butanol → HCID 21199124, compound

HRID 1066284Notes

Reaction equation

HRID 1066284 reaction equation
[CH2:1](O)[CH2:2][CH2:3]C.[H-].[Na+].[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:31])=[C:13]([C:29]=1[CH3:30])[C:14]([C:16]1[C:21](C)=[CH:20][C:19]([O:23][CH3:24])=[C:18]([O:25][CH3:26])[C:17]=1[O:27][CH3:28])=[O:15]>C(COC)OC>[Br:8][C:9]1[C:29]([CH3:30])=[C:13]([C:12]([CH3:31])=[CH:11][CH:10]=1)[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:23][CH3:24])=[C:18]([O:25][CH3:26])[C:17]=1[O:27][CH2:28][CH2:1][CH2:2][CH3:3])=[O:15]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 24758Sodium hydrideHCID 10949234HCID 10949234, compound

Product 1

HCID 21199124HCID 21199124, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of n-butanol (5 ml) and sodium hydride (60% in oil, 20 mmol) is stirred until the formation of H2 gas ceases. A mixture of 1C (2.0 g, 5.0 mmol) and dimethoxyethane (15 ml) is added to the resulting reaction mixture. Subsequently, the reaction mixture is heated to 90° C. with stirring for 14 hours and dimethoxyethane is distilled off. A mixture of water and ethyl acetate (1:1 v/v; 100 ml) is then slowly added at room temperature. The organic phase is separated, concentrated and the residue is purified by column chromatography (petrol ether: ethyl acetate, 90:10 v/v) yielding the pure product as a yellow oil, 1.7 g (78.3%).

Workup

  1. additionis added to the resulting reaction mixture
  2. stirringwith stirring for 14 hours
  3. distillationdimethoxyethane is distilled off
  4. additionA mixture of water and ethyl acetate (1:1 v/v; 100 ml)
  5. additionis then slowly added at room temperature
  6. customThe organic phase is separated
  7. concentrationconcentrated
  8. customthe residue is purified by column chromatography (petrol ether: ethyl acetate, 90:10 v/v)

Sources & evidence

ORD record
ord-b927853de59045fcb36cbb6497d500ce
Source dataset
uspto-grants-2001_06
Patent number
US06242498B1

Reaction notes

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