Azidotrimethylsilane → HCID 22630139, compound

HRID 2307089Notes

Reaction equation

HRID 2307089 reaction equation
[CH3:1][C:2](O)([CH3:14])[CH:3]=[C:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]([CH3:13])([CH3:12])[CH2:5]1.[Si]([N:20]=[N+:21]=[N-:22])(C)(C)C>C1C=CC=CC=1>[N:20]([C:2]([CH3:14])([CH3:1])[CH:3]=[C:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]([CH3:13])([CH3:12])[CH2:5]1)=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 22630121HCID 22630121, compound

Product 1

HCID 22630139HCID 22630139, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
7.5 °C

Procedure

BF3Et2O (0.3 ml, 2.4 mmol) was added to a solution of alcohol 29 (0.42 g, 2 mmol) and TMSN3 (0.31 ml, 2.4 mmol) in benzene (4.5 ml) during 3 min, while cooling with an ice bath. The reaction mixture was stirred at 5-10° C. for 1 h and filtered through a short silica gel column. The solution was evaporated and the residue was purified by flash chromatography on silica gel (light petroleum ether) to give 30 (0.30 g, 64%) as a colorless oil. 1H-NMR (CDCl3, TMS): 0.92 and 0.98 (total 12H, both s, c-Hex-3,5-CH3); 1.27 (2H, s, c-Hex-4-CH2); 1.40 (6H, s, —C(CH3)2N3); 1.85 and 2.23 (both 2H, both s, c-Hex-2,6-CH2) and 5.27 ppm (1H, s, ═CH—).

Workup

  1. temperaturewhile cooling with an ice bath
  2. filtrationfiltered through a short silica gel column
  3. customThe solution was evaporated
  4. customthe residue was purified by flash chromatography on silica gel (light petroleum ether)

Sources & evidence

ORD record
ord-3141194c4da4417d98d3b39a8f4a66b0
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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