Dimethylformamide → ({[5-(2-Azidoethyl)-2,3-dichlorophenyl]methyl}oxy)(1,1-dimethylethyl)dimethylsilane

HRID 337590Notes

Reaction equation

HRID 337590 reaction equation
CN(C=O)C.CS(O[CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:16]([Cl:28])=[C:15]([Cl:29])[CH:14]=1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CCOCC>[N:30]([CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([Cl:29])[C:16]([Cl:28])=[C:17]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:18]=1)=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 866516682-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate

Product 1

HCID 86651669({[5-(2-Azidoethyl)-2,3-dichlorophenyl]methyl}oxy)(1,1-dimethylethyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a DMF (0.4 M) solution of 2-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate (1 eq.) from Step 5, Amine 26 was added at RT sodium azide (5 eq.). The resulting solution was stirred at RT for 12 h and then at 80° C. for 3 h. The reaction mixture was then diluted with ether and washed with water. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a pink oil.

Workup

  1. waitat 80° C. for 3 h
  2. washwashed with water
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5a8506b38f1142b391b14139d03e4133
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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