Water → Diisopropyl Ether

HRID 1374094Notes

Reaction equation

HRID 1374094 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-0f1414164bbe4fd3a0570694eb46d72a
Source dataset
uspto-grants-2007_01
Patent number
US07164017B2

Reaction notes

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