Sodium Chloride → Diisopropyl Ether

HRID 411147Notes

Reaction equation

HRID 411147 reaction equation
[NH2:1][CH2:2][CH:3]([OH:14])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[C:15](O[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(OC(C)(C)C)=O.[Na+].[Cl-]>C1COCC1>[CH:6]([O:5][CH:4]([CH3:3])[CH3:15])([CH3:7])[CH3:13].[C:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][CH:3]([OH:14])[CH2:2][NH:1][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[CH:7][CH:8]=1)#[N:11]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 167827394-[(3-Amino-2-hydroxypropyl)oxy]benzonitrile

Product 2

HCID 7914Diisopropyl EtherHCID 21867654Tert-butyl 3-(4-cyanophenoxy)-2-hydroxypropylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) solution of 4-[(3-amino-2-hydroxypropyl)oxy]benzonitrile (from step (ii) above; 44.6 g, 0.23 mol) in THF:H,O (1.5 L of 1:1) was treated with di-tert-butyl dicarbonate (53 g, 0.24 mol). The mixture was stirred at rt overnight, after which NaCl was added and the resulting organic layer separated. The water layer was extracted with ether and the combined organics were dried and concentrated in vacuo. The resulting oil (70 g) was filtered through a plug of silica, and then crystallised from diethyl ether:di-iso-propyl ether to yield 50 g of the sub-title compound.

Workup

  1. customthe resulting organic layer separated
  2. extractionThe water layer was extracted with ether
  3. customthe combined organics were dried
  4. concentrationconcentrated in vacuo
  5. filtrationThe resulting oil (70 g) was filtered through a plug of silica
  6. customcrystallised from diethyl ether

Sources & evidence

ORD record
ord-37c2ffe813fd4db1ae26ae4d5e8383b6
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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