Azidotrimethylsilane → HCID 86616049, compound

HRID 602940

Reaction equation

HRID 602940 reaction equation
[CH:1]([Si:4]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[O:5][C:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=2[F:20])[CH2:8][CH:7]=1)([CH3:3])[CH3:2].I(C1C=CC=CC=1)=O.[N:35]([Si](C)(C)C)=[N+:36]=[N-:37]>ClCCl>[N:35]([CH:8]1[CH:9]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=2[F:20])[CH2:10][CH2:11][C:6]([O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:26])[CH3:25])=[CH:7]1)=[N+:36]=[N-:37]

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 92125IodosylbenzeneHCID 67065786HCID 67065786, compound

Product 1

HCID 86616049HCID 86616049, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a three-neck flask, a stirred solution of triisopropyl {[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane (26.06 g, 0.068 mol) in dichloromethane (260 mL) was cooled to −15° C. and treated with iodosobenzene (19.5 g, 0.089 mol) in four portions followed by azidotrimethylsilane (24 mL, 0.116 mol) while maintaining the temperature below −10° C. Stirring was continued for 1.5 h. The reaction mixture was allowed to warm to room temperature briefly, then cooled again back to −15° C. and filtered. The filtrate was evaporated under vacuum below 25° C. to give the title compound which was used directly in the next step.

Workup

  1. temperaturewhile maintaining the temperature below −10° C
  2. temperaturecooled again back to −15° C.
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum below 25° C.

Sources & evidence

ORD record
ord-3dab32a08fdc41359b416c82f0dac8f5
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Linked notes

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