Water → HCID 22630136, compound

HRID 2307079Notes

Reaction equation

HRID 2307079 reaction equation
[CH2:1]([C:4]1(O)[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]([CH3:13])([CH3:12])[CH2:5]1)[CH:2]=[CH2:3].[N:15]([Si](C)(C)C)=[N+:16]=[N-:17].B(F)(F)F.O>C1C=CC=CC=1>[CH2:1]([C:4]1([N:15]=[N+:16]=[N-:17])[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]([CH3:13])([CH3:12])[CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6356Boron trifluorideHCID 78378AzidotrimethylsilaneHCID 22630140HCID 22630140, compound

Product 1

HCID 22630136HCID 22630136, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of cyclohexanol 8 (1.96 g, 10 mmol) in dry benzene (20 ml) under argon was added azidotrimethylsilane (12 mmol). To this cooled (5° C.) solution was slowly added BF3*OEt2 (12 mmol) via syringe within 20 min. The mixture was stirred for 6 h, then water was slowly added. The organic layer was separated and washed with saturated aqueous NaHCO3, and with brine, and dried over MgSO4. Filtration and evaporation of the solvent keeping the temperature below 25° C. gave an oil which was separated by column chromatography on silica gel (light petroleum ether). A fraction with Rf 0.85 (hexane) was collected. Evaporation of the solvent provided 9 as a colorless oil (0.26 g, 11.7%). 1H NMR (CDCl3, TMS): 0.89 (6H, s, 3,5-CH3eq); 0.90 (1H, d, 14 Hz, 4-CHax); 1.05 (2H, d, 14 Hz, 2,6-CHax); 1.18 (6H, s, 3,5-CH3ax); 1.37 (1H, d, 14 Hz, 4-CHeq); 1.60 (2H, d, 14 Hz, 2,6-CHeq), 2.29 (2H, d, 7 Hz, CH2C═); 4.95-5.25 (2H, m, ═CH2) and 5.65-6.15 ppm (1H, m, ═CH).

Workup

  1. customwithin 20 min
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialwith brine, and dried over MgSO4
  5. filtrationFiltration and evaporation of the solvent
  6. customthe temperature below 25° C.
  7. customgave an oil which
  8. customwas separated by column chromatography on silica gel (light petroleum ether)
  9. customA fraction with Rf 0.85 (hexane) was collected
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-94ef5c731b2a44e18146a1e88e2c87c2
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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