Water → Diisopropyl Ether

HRID 500479Notes

Reaction equation

HRID 500479 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.O.[C:16](O[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])(OC(C)(C)C)=O.[Na+].[Cl-]>C1COCC1>[CH:6]([O:5][CH:4]([CH3:3])[CH3:16])([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:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[CH:7][CH:8]=1)#[N:11]

Participants

7

Reactant 4

HCID 962WaterHCID 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:H2O (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-27b7a1eac6274a0c887a1d0f639b4113
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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